Chloro-5-methylquinoline

A most remarkable reaction of Grignard reagents with a l-(oxazolidin-2-yl)naphthalene has been described, in which addition to the aromatic ring occurs, whereas organolithium, organocerium or organocopper reagents all attack the oxazolidine 2-position [20]  

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ChLorofluorocarbene generated by the thermal decomposition of dichlorofluoro-methylphenylmercury reacts with 2,3-dimethylindole to give 3-fluoro-2,4-di-methylquinoline, 3-chloro-2,4-dimethylqumoline and 3-(chlorofluoromethyl)-2,3-dimethylindole [f] (equation 1). Similar results are obtained when the chloro-fluorocarbene is generated from dichlorofluoromethane by base-catalyzed de-hydrohalogenation using a phase-transfer catalyst in an aqueous-organic solvent system [21 (equation 1). 

The Reimer-Tiemann reaction has also been used to formylate 2,5-dimethylpyrrole and its iV-methyl derivative and indoles having methyl, methoxyl, and phenyl substituents. Significantly, 3-methylindole gave only 3-chloro-4-methylquinoline. ... 

Chloroaniline was reacted with diethyl acetylmalonate at room temperature in vacuo over anhydrous CaCl2 for 10 days. The resulting cro-tonate (803) was cyclized in boiling diphenyl ether for 40 min to give 7-chloro-4-hydroxy-2-methylquinoline-3-carboxylate in 17% yield (73USP3755332). 

When the reaction mixture of 4-chloroaniline, triethyl orthoformate, and isopropylidene methylmalonate in Dowtherm A was heated slowly, stirred to reflux, and maintained at reflux for 3 minutes, 6-chloro-4-hydroxy-3-methylquinoline (1167) was obtained (69BRP1147760). 

Chloro-2-methylquinoline, AQ82 [2-(L-Chloromethylth iazolyl)]-benzene, AQ83... 

Diphenylphosphino-l -naphthyl)isoquinoline forms P,N-chelate 245 (93T(A)743). 8-Diphenylphosphinoquinoline with trans-chloro(l-naphthyl)bis(triphenylphosphine)nickel gives chelate 246 (02NJC1474). 8-Dimethylphosphinoquinoline and -2-methylquinoline with [(r 4-cod) Pd(Me)Cl] give [Pd(T)2(N,P)-L)(Me)Cl], which with 2,6-Me2C6H3NC... 

Quinoline derivatives (60) have been synthesized by the reaction of 5-alkyl-l,3,4-thia-diazol/oxadiazol-2-thiols with 7-chloro-6-uoro-2,4-dimethylquinoline and by the reaction of 2-hydroxy-l,4-naphthoquinone with 2-chloro-3-formyl-4-methyl/ 6-methyl/7-methyl/8-methylquinolines, respectively, on basic alumina using micro-waves (Kidwai et al., 2000). 

Compound 410 was prepared from 4-chloro-3-chloromethyl-5,8-di-methoxy-2-methylquinoline. In hot acetic acid the furan ring was formed and dichromate oxidation gave the product (6SMI1). 

Pyrazolo[3,4-Z)]pyridines, the 7-chloro-6-fluoro-2,4-dimethylquinoline and its mercapto-thiadiazolyl or oxadiazolyl quinolines 21 were prepared via Diels-Alder reaction conversion of methyl 2-(3-oxo-3-phenylpropenylamino)benzoate into 3-benzoyl-l.S -quinolin-4-one 22 . A mixture of aniline derivatives and malonic ester gave a variety of 3-aryl-4-hydroxyquinolin-2(l//)-ones 23. Condensation of isatins with ketones afforded quinoline-4-carboxylic acids. 2-Aryl-l,2,3,4-tetrahydro-4-quinolinones 22 and carbazolylquinolone were also prepared. The substitution of 2-chloroquinoline gave the 2-substituted quinolines. Basic alumina has catalyzed the C-C bond formation between 2-hydroxy-1,4-naphthoquinone and 2-chloroquinoline derivative to give 21. Reaction of organic halides with 8-hydroxyquinolines gave the respective ethers. The azodye derivatives of 21 were prepared in the absence of solvent. Silica gel catalyzed the formation of 2-ketomethylquinolines from reaction of 2-methylquinolines with acyl chlorides. 

When thionyl chloride is heated in an atmosphere of argon with 4-methyl-quinoline for 20 h, the methyl group and the pyridine ring are chlorinated. The mechanism appears to be complex but the product has a fused dithiolone ring. However, treatment of 2-chloro-4-methylquinoline with thionyl chloride does not yield a dithioloquinolinone. 

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