6-Fluoro-2-methylquinoline

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). 

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. 

Rapid chloiinadoii of side-chain Me group of 2-fluoro-4-methylquinoline 72b is reported using sodium hypochlorite under microwave irradiation (Scheme 78) [109],... 

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