Tag: M.W:100-200

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《8-(3-Diethylaminopropylamino)isoquinoline》. Authors are Robinson, Richard A..The article about the compound:Isoquinolin-6-olcas:7651-82-3,SMILESS:OC1=CC2=C(C=NC=C2)C=C1).Product Details of 7651-82-3. Through the article, more information about this compound (cas:7651-82-3) is conveyed.

cf. preceding 2 abstracts Isoquinoline sulfate (78 g.), preheated to 300°, treated (5 min.) with 60 g. 60% oleum, and heated 5 min. at 300°, gives 35% of the 5-sulfonic acid (as the Ca salt) and 55 g. of mixed Na isoquinolinesulfonates which, on fusion with NaOH (10 min. at 210°), give 15% 8-hydroxyisoquinoline (I), m. 213° (picrate, m. 285°). I (10 g.), 60 mL. concentrated NH4OH, and 14 g. SO2, heated 6 h. at 150-60°, give 8.5 g. 8-aminoisoquinoline (II), m. 174°. II (20 g.), 120 g. Et2N(CH22)3NH2, 150 mL. H2O, and 30 g. SO2, heated at reflux temperature 36 h. under 3 in. pressure, give 18 g. 8-(3-diethylaminopropylamino)isoquinoline, yellow, m. 231°. 6-Methoxyisoquinoline (0.3 g.) and 20 mL. 48% HBr, refluxed 2 h., give 6-hydroxyisoquinoline, m. 220°; HCl salt m. 175°.

Here is just a brief introduction to this compound(7651-82-3)Product Details of 7651-82-3, more information about the compound(Isoquinolin-6-ol) is in the article, you can click the link below.

Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Anomalies in the reduction of 2,2′-diacetylbiphenyl》. Authors are Hall, D. Muriel; Ladbury, Joan E.; Lesslie, Mary S.; Turner, E. E..The article about the compound:Isoquinolin-6-olcas:7651-82-3,SMILESS:OC1=CC2=C(C=NC=C2)C=C1).COA of Formula: C9H7NO. Through the article, more information about this compound (cas:7651-82-3) is conveyed.

2,2′-Diacetylbiphenyl (I) formed 9,10-dimethylphenanthrene (II) on Clemmensen reduction. With LiAlH4 I gave 2 diastereoisomeric 2,2′-di(1-hydroxyethyl)biphenyls, (III) and (IV). III and IV reacted normally with HBr and, by the action of refluxing quinoline (V) on the resulting mixture of isomerides, 2,2′-divinylbiphenyl (VI) was prepared Reduction of I under Huang-Minlon conditions gave 2-methyl-3,4,5,6-dibenzocyclohepta-1,3,5-triene (VII). 2,2′-Di-(1-hydroxy-1-methylethyl)biphenyl (VIII) was dehydrated in 3 ways, to give 2,7,7-trimethyl-3,4,5,6-dibenzocyclohepta-1,3,5-triene (IX), 2,2′-diisopropenylbiphenyl (X), or 2,7-dihydro-2,2,7,7-tetramethyl-3,4,5,6-dibenzoxepin (XI). It had been thought that the Clemmensen reduction of I may possibly serve as a route to 2,2′-diethylbiphenyl (XII), but the above results indicated that XII could not be prepared by this method. Finely ground phenanthraquinone (84 g.) was added to MeMgI from 39 g. Mg and MeI and after addition of 500 cc. C6H6 the mixture was refluxed 2 hrs. and 6.5 g. of starting material was recovered by use of NaHSO3. The Et2-C6H6 washed with brine, distilled to a volume of 300 cc. and cooled gave 75 g. 9,10-dihydro-9,10-dihydroxy-9,10-dimethylphenanthrene (XIII), m. 163-4°. The use of 6 moles MeMgI did not improve the yield of XIII and greatly extended the time of operation. XIII (38 g.) in 380 cc. AcOH treated at 70° during 10 min. with 16 g. CrO3 in 160 cc. H2O, the mixture left 10 min. at 70°, and the crude product purified gave 89% I, m. 93-4° (from cyclohexane). I and 4 moles of MeMgI gave 80% VIII, b. 320°, m. 139-40° (from alc.). I (28 g.) and HCl refluxed 6 hrs. in the presence of Zn-Hg gave 24.5 g. (crude) II, m. 144°; picrate, m. 192-3°. The material was identical with a specimen of authentic II. I (11.9 g.) heated 1 hr. with LiAlH4 in Et2O and the solid repeatedly recrystallized from C6H6 gave III as prisms, m. 147.5-9.0°, and IV as long prisms, m. 153-5°. III (1 g.) heated 2.5 hrs. with 15 cc. 20% H2SO4 gave 2,7-dihydro-2,7-dimethyl-3,4,5,6-dibenzoxepin (XIV), m. 77-80° (from MeOH). IV similarly treated but with 7 hrs. heating gave XIV, m. 74-8°. Thus the product seemed to be a mixture III gave XIV as the main product but IV more obviously gave a mixture Either III or IV or a mixture of both heated 15 min. with a large excess of HBr gave about 20% 2,2′-di(1-bromoethyl)biphenyl (XV), m. 88-92°. Second crop m. 71-9°. These also gave VI when dehydrobrominated with V. A solution of XV in V refluxed 5 min. gave VI, m. 80-1°. The m.p. remained unchanged after several months. Hydrogenation in alc. solution with PtO2 and H gave XII, b13.5 139-40°, nD25 1.5626. XII(21 g.), 35.6 g. (2 moles) N-bromosuccinimide, and 0.1 g. Bz2O2 in dry CCl4 refluxed 3 hrs. yielded 25.5 g. (crude) XV, m. 87-90°. I(20 g.), 34 g. NaOH, 34 cc. 85% aqueous H2NNH2, and 500 cc. triethylene glycol refluxed 2 hrs., H2O and excess H2NNH2.H2O removed until the temperature reached 195°, then refluxed 4 hrs., and the residual product distilled gave 10 g. pure VII, m. 49.5-50.5°. The residue treated with picric acid yielded 0.5 g. II picrate. VII (7.5 g.)in AcOH shaken with H and Pd yielded 2-methyl-3,4,5,6-dibenzocyclohepta-3,5-diene (XVI) as an oil, b1 120°, nD25 1.6102. Proof of structure of XVI was confirmed by the ultraviolet absorption spectrum. Further proof for the structure of VII came from its behavior on oxidation. VII (0.513 g.) in 2.5 cc. xylene refluxed 5.5 hrs. with 0.304 g. SeO2 and the residue treated with 2,4-dinitrophenylhydrazine gave 2-methyl-7-oxo-3,4,5,6-dibenzocyclohepta-1,3,5-triene 2,4-dinitrophenylhydrazone, m. 252° (decomposition) (from C6H6-ligroine). VII (1.6 g.) in AcOH heated 1.75 hrs. with 7 g. Na2Cr2O7 in AcOH yielded phenanthraquinone (XVII), m. 208-9°; quinoxaline derivative (with o-phenylenediamine), m. 222-3°. Chromatography of the residual product on Al2O3 gave 2-acetyl-2′-formylbiphenyl (XVIII). The Na2CO3 washings acidified gave a gum which solidified to 2′-acetylbiphenyl-2-carboxylic acid, m. 120-1° (from alc. and cyclohexane). VI (1 g.) in AcOH similarly oxidized with Na2Cr2O7 in AcOH gave XVII. This was a test for the bridged biphenyl system. I (5 g.) and 2.5 cc. 85% H2NNH2.H2O in alc. kept at 60-40° overnight gave 0.2 g. II; addition of NH3 to the filtrate precipitated 2.6 g. 3,8-dimethyl-4,5,6,7-dibenzo-1,2-diazocine (XIX), prisms, m. 167-8° (from aqueous alc.). In other preparations the solution was refluxed for several hrs. to give more II and less XIX. XIX (0.3 g.) and 15 cc. dilute H2SO4 refluxed 1 hr. gave I, m. 91-3°. XIX (0.6 g.) heated 3.5 hrs. at 195° with 0.7 g. NaOH and 11 cc. triethylene glycol yielded 0.5 g. crude II, which was purified from alc. XIX remained unaffected by hot aqueous-alc. H2NNH2.H2O or NaOH or when heated above its m.p. alone or with Cu bronze. Meerwein-Ponndorf-Verley reduction of I was attempted but the product was a mixture and no pure compounds could be isolated. VIII (2 g.) refluxed 1 hr. with 60 cc. 4N H2SO4 gave XI, m. 92-3° (from MeOH). A mixture of 10 g. VIII and 0.1 g. naphthalene-2-sulfonic acid heated 15 min. at 140° gave IX, m. 100-1°. A suspension of IX or of XI in HBr refluxed 1 hr. gave IX. IX (10 g.) in AcOH-EtOAc shaken with H in the presence of PtO2 for several hrs. yielded 9.5 g. 2,2,7-trimethyl-3,4,5,6-dibenzocyclohepta-3,5-diene, prisms, m. 67-71° (from alc.). IX (5 g.) refluxed at 320° with a little Cu bronze and activated Al2O3 and the b.p. dropped within 10 min. to 295° gave 3 g. X, b5 136°, nD21 1.5890. A small amount of XI was also isolated. An AcOH solution of X was shaken 1 hr. with H and PtO2 to give 2,2′-diisopropylbiphenyl. X (1.3 g.) refluxed 1.5 hrs. with 20 cc. HBr gave IX. X (1 g.) refluxed 5 hrs. with 50% H2SO4 yielded 0.5 g. IX. VI (0.5 g.) and HBr refluxed 1.5 hrs. gave XV. IX (1.1 g.) in AcOH and 5.6 g. Na2Cr2O7 heated 1.75 hrs. and the residue treated with o-phenylenediamine gave the quinoxaline derivative of XVII. The ligroine extract yielded XVIII, m. 84°. Dinitrophenylhydrazone formation was accompanied by cyclization; 7-oxo-3,4,5,6-dibenzocyclohepta-1,3,5-triene 2,4-dinitrophenylhydrazone, m. about 208° (decomposition), was isolated. The Na2CO3 washings were acidified to give a gum from which 2 impure crystallization acids were isolated. Quantities were too small for further investigation.

Compound(7651-82-3)COA of Formula: C9H7NO received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(Isoquinolin-6-ol), if you are interested, you can check out my other related articles.

Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Computed Properties of C8H12N2O. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 5-Methyl-1-propyl-1H-pyrazole-4-carbaldehyde, is researched, Molecular C8H12N2O, CAS is 890652-02-5, about Identification of small-molecule inhibitors of Trypanosoma cruzi replication. Author is Germain, Andrew R.; Carmody, Leigh C.; Dockendorff, Chris; Galan-Rodriguez, Cristina; Rodriguez, Ana; Johnston, Stephen; Bittker, Joshua A.; MacPherson, Lawrence; Dandapani, Sivaraman; Palmer, Michelle; Schreiber, Stuart L.; Munoz, Benito.

We report the outcome of a high-throughput small-mol. screen to identify novel, nontoxic, inhibitors of Trypanosoma cruzi, as potential starting points for therapeutics to treat for both the acute and chronic stages of Chagas disease. Two compounds were identified that displayed nanomolar inhibition of T. cruzi and an absence of activity against host cells at the highest tested dose. These compounds have been registered with NIH Mol. Libraries Program (probes ML157 and ML158).

Compound(890652-02-5)Computed Properties of C8H12N2O received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(5-Methyl-1-propyl-1H-pyrazole-4-carbaldehyde), if you are interested, you can check out my other related articles.

Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Safety of 2-Cyano-2-methylpropanoic acid. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-Cyano-2-methylpropanoic acid, is researched, Molecular C5H7NO2, CAS is 22426-30-8, about β-Aryl nitrile construction via palladium-catalyzed decarboxylative benzylation of α-cyano aliphatic carboxylate salts. Author is Shang, Rui; Huang, Zheng; Xiao, Xiao; Lu, Xi; Fu, Yao; Liu, Lei.

The palladium-catalyzed decarboxylative benzylation of α-cyano aliphatic carboxylate salts with benzyl electrophiles was discovered. This reaction exhibits good functional group compatibility and proceeds under relatively mild conditions. A diverse range of quaternary, tertiary and secondary β-aryl nitriles can be conveniently prepared by this method.

Compound(22426-30-8)Safety of 2-Cyano-2-methylpropanoic acid received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(2-Cyano-2-methylpropanoic acid), if you are interested, you can check out my other related articles.

Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Gazzetta Chimica Italiana called The action of hydroxylamine on γ-pyrone, Author is Parisi, Federico; Bovina, Pietro; Quilico, Adolfo, which mentions a compound: 27828-71-3, SMILESS is O=C(O)C1=CN=CC(O)=C1, Molecular C6H5NO3, Recommanded Product: 5-Hydroxynicotinic acid.

Treatment of γ-pyrone (I) with HONH2 gave a substance, C5H6N2O2 (II), to which was ascribed the structure 4-hydroxylaminopyridine 1-oxide. I (17.5 g.) in 20 ml. H2O and 13.5 g. HONH2.HCl in 50 ml. H2O containing 13.5 g. NaHCO3 kept in the dark 2-3 days at 20°, the crystalline product washed with H2O and desiccated in vacuo over CaCl2 yielded 76% II, m. 220°. II was unstable in aqueous alkali with formation of an intensely red solution Finely ground II (0.5 g.) in 40 ml. H2O hydrogenated with 0.2 g. PtO2, the mixture treated with 8 ml. N HCl and the filtered solution saturated with KOH, extracted with Et2O and the product recrystallized from C6H6 gave 4-H2NC5H4N, m. 160-1°, also prepared by reduction of 4-O2NC5H4NO. II (0.25 g.) in 20 ml. 20% H2SO4 stirred with instantaneous addition of 0.125 g. KMnO4 in 15 ml. H2O, extracted with CHCl3 and the residue on evaporation taken up in 8 ml. hot PhMe, the cooled tepid solution filtered, diluted with an equal volume of petr. ether and refrigerated gave green needles of 4-ONC5H4N(O) (III), m. 138-9°. II (1.0 g.) in 50 ml. H2O boiled 3-4 min. with addition of decolorizing C, the filtered solution kept 12 hrs. at 20° and the orange-yellow product repeatedly crystallized from alc. and H2O gave 0.15-0.20 g. 4,4′-azoxypyridine 1,1′-dioxide (IV), m. 236-7°. The mother liquors evaporated and the residue recrystallized from alc. yielded 4,4′-azopyridine 1,1′-dioxide (V), m. 246-7°. II (0.10 g.) in 10 ml. cold 20% H2SO4 treated with 0.10 g. III in 10 ml. H2O, the mixture kept 16 hrs. at 20° and adjusted to pH 6.5-7.0 with 20% NaOH and NaOAc gave IV, also produced by oxidation of II in AcOH with 30% H2O2. AcOH (15 ml.) containing 1 g. 4-O2NC5H4NO treated portionwise with 0.75 powd. Zn with external cooling the mixture kept 2 days and the filtered solution adjusted to pH 6.5-7.0, repeatedly extracted with CHCl3 gave 60 mg. IV, m. 235-6° (H2O-alc.). II (1.0 g.) triturated with 3-4 ml. aqueous 10% KOH with characteristic crepitation and the bright red product crystallized from 20 ml. hot H2O gave V, m. 246-7° (H2O). IV (0.5 g.) in 40 ml. H2O hydrogenated with 0.2 g. PtO2 with addition of 12 ml. 0.5N HCl, the filtered solution partially neutralized with 10 ml. 0.5N NaOH and the washed precipitate dried in vacuo gave the unstable 4,4-hydrazo pyridine (VI), m. above 270°, rapidly turning rose-violet, also produced by hydrogenation of V. The above filtered solution evaporated in vacuo and the residue recrystallized from alc. gave 90% VI.2HCl, m. 190°, also prepared more conveniently by passage of dry HCl through alc. VI. VI.2HCl in H2O treated with 10% excess 0.5N NaOH and boiled with atm. oxidation to complete soluble, the solution cooled and filtered from the main product, the mother liquor extracted with Et2O and the combined crops crystallized from H2O gave trans-4,4′-azo pyridine (VII), m. 108-9°. VII in absolute alc. saturated with dry HCl gave the di-HCl salt. VII (0.5 g.) in 20 ml. AcOH refluxed 12 hrs. with 20 ml. 36% H2O2, the mixture concentrated in vacuo, diluted with H2O and extracted with CHCl3, the dried extract evaporated in vacuo and the concentrate evaporated spontaneously, the residue taken up in H2O and adjusted to pH 7.0 with aqueous Na2CO3, extracted with CHCl3 and the product recrystallized from alc. or H2O gave IV. The mechanism of the formation of IV, a prime example of the reaction of the CO group of a pyrone with HONH2, was discussed.

Here is just a brief introduction to this compound(27828-71-3)Recommanded Product: 5-Hydroxynicotinic acid, more information about the compound(5-Hydroxynicotinic acid) is in the article, you can click the link below.

Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: Isoquinolin-6-ol(SMILESS: OC1=CC2=C(C=NC=C2)C=C1,cas:7651-82-3) is researched.Application In Synthesis of Aluminum triquinolin-8-olate. The article 《Synthesis of Indole-Dihydroisoquinoline Sulfonyl Ureas via Three-Component Reactions》 in relation to this compound, is published in Synthesis. Let’s take a look at the latest research on this compound (cas:7651-82-3).

Isoquinolines activated with sulfamoyl chlorides were reacted with indoles in a 3-component reaction to generate a library of dihydroisoquinoline derivs, e.g., I. Using a differential protecting group strategy, products were further derivatized. Synthesis of isoquinoline starting materials using several different methods was also described.

Here is just a brief introduction to this compound(7651-82-3)Recommanded Product: 7651-82-3, more information about the compound(Isoquinolin-6-ol) is in the article, you can click the link below.

Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 7651-82-3, is researched, Molecular C9H7NO, about Hueckel molecular orbital [HMO] study of monohydroxypyridines and their benzoderivatives, the main research direction is Hueckel MO hydroxy pyridine; quinoline Hueckel MO; isoquinoline Hueckel MO; acridine Hueckel MO; phenanthridine Hueckel MO.Related Products of 7651-82-3.

Fifteen monohydroxy derivatives of pyridine, quinoline, isoquinoline, acridine, and phenanthridine were studied by simple HMO method. These compounds, in which possibility of keto-enol tautomerism must be considered can participate in chem. reactions in two mol. forms. The simple HMO method, despite its strongly approximative character, satisfactorily interprets exptl. data of the chem. properties of studied compounds The quantum-chem. approach, based on estimation of values of chem. reactivity indexes, fails to give a true picture of the reactivity of aromatic ring of benzo derivatives, in the HMO models of which Coulomb or exchange integrals are not changed on these rings as a result of the introduction of a substituent or an heteroatom. The results show that in most of the reactions studied tautomerism does not affect significantly the order of reactivity of the individual positions of the π-electrone system.

Here is just a brief introduction to this compound(7651-82-3)Related Products of 7651-82-3, more information about the compound(Isoquinolin-6-ol) is in the article, you can click the link below.

Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 7651-82-3, is researched, SMILESS is OC1=CC2=C(C=NC=C2)C=C1, Molecular C9H7NOJournal, Article, Journal of Medicinal Chemistry called Novel Vanilloid Receptor-1 Antagonists: 2. Structure-Activity Relationships of 4-Oxopyrimidines Leading to the Selection of a Clinical Candidate, Author is Doherty, Elizabeth M.; Fotsch, Christopher; Bannon, Anthony W.; Bo, Yunxin; Chen, Ning; Dominguez, Celia; Falsey, James; Gavva, Narender R.; Katon, Jodie; Nixey, Thomas; Ognyanov, Vassil I.; Pettus, Liping; Rzasa, Robert M.; Stec, Markian; Surapaneni, Sekhar; Tamir, Rami; Zhu, Jiawang; Treanor, James J. S.; Norman, Mark H., the main research direction is oxopyrimidine TRPV1 antagonist preparation SAR.Quality Control of Isoquinolin-6-ol.

A series of novel 4-oxopyrimidine TRPV1 antagonists was evaluated in assays measuring the blockade of capsaicin or acid-induced influx of calcium into CHO cells expressing TRPV1. The investigation of the structure-activity relationships in the heterocyclic A-region revealed the optimum pharmacophoric elements required for activity in this series and resulted in the identification of subnanomolar TRPV1 antagonists. The most potent of these antagonists were thoroughly profiled in pharmacokinetic assays. Optimization of the heterocyclic A-region led to the design and synthesis of 23 (I), a compound that potently blocked multiple modes of TRPV1 activation. Compound 23 was shown to be effective in a rodent “”on-target”” biochem. challenge model (capsaicin-induced flinch, ED50 = 0.33 mg/kg p.o.) and was antihyperalgesic in a model of inflammatory pain (CFA-induced thermal hyperalgesia, MED = 0.83 mg/kg, p.o.). Based on its in vivo efficacy and pharmacokinetic profile, compound 23 (N-{4-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-acetamide; AMG 517) was selected for further evaluation in human clin. trials.

Here is just a brief introduction to this compound(7651-82-3)Quality Control of Isoquinolin-6-ol, more information about the compound(Isoquinolin-6-ol) is in the article, you can click the link below.

Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Application of 27828-71-3. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 5-Hydroxynicotinic acid, is researched, Molecular C6H5NO3, CAS is 27828-71-3, about Tetraaquabis(5-hydroxynicotinato-κN)cadmium(II). Author is Jiang, Mei-Xiang; Feng, Yun-Long.

The title compound, [Cd(C6H4NO3)2(H2O)4], was obtained by the reaction of cadmium chloride with 5-hydroxynicotinic acid. The CdII atom is located on an inversion center and is coordinated by two N atoms from two 5-hydroxynicotinic acid ligands and four water mols. in a distorted octahedral geometry. The structure is stabilized by intermol. O-H…O hydrogen bonds, forming a three-dimensional network. Crystallog. data are given.

Here is just a brief introduction to this compound(27828-71-3)Application of 27828-71-3, more information about the compound(5-Hydroxynicotinic acid) is in the article, you can click the link below.

Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, European Journal of Organic Chemistry called Cleavage of aromatic methyl ethers by chloroaluminate ionic liquid reagents, Author is Kemperman, Gerardus J.; Roeters, Theodorus A.; Hilberink, Peter W., which mentions a compound: 7651-82-3, SMILESS is OC1=CC2=C(C=NC=C2)C=C1, Molecular C9H7NO, Recommanded Product: 7651-82-3.

The authors discovered serendipitously that chloroaluminate ionic liquids can cleave aromatic Me ethers under surprisingly mild conditions. Three ionic liquids, viz. [Me3NH][Al2Cl7], [BMIM][Al2Cl7] (BMIM = 1-butyl-3-methylimidazolium), and [EMIM][Al2Cl6I] (EMIM = 1-ethyl-3-methylimidazolium), and AlCl3 were prepared and compared in the selective demethylation of 4,5-dimethoxyindanone at the 4-methoxy-function. The ionic liquids exhibited a remarkably high selectivity (96:4) in comparison with AlCl3 (70:30). The reaction time was drastically shortened when the ionic liquids were used. The three ionic liquids displayed the same reactivity in the demethylation of 4,5-dimethoxyindanone. Considering the lower cost and the bulk availability of the precursors of [Me3NH][Al2Cl7], this is the most attractive ionic liquid from an industrial point of view. To make the large-scale application of [Me3NH][Al2Cl7] feasible, the authors have developed a safe upscalable method for its preparation Also, the scope of ether cleavage by the ionic liquid reagent [Me3NHTMAH][Al2Cl7] was studied and aromatic Me-, allyl-, and benzyl-ether cleavage is applicable to a variety of heterocyclic compounds

When you point to this article, it is believed that you are also very interested in this compound(7651-82-3)Recommanded Product: 7651-82-3 and due to space limitations, I can only present the most important information.

Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method