8- methylquinoline halides

The Skraup synthesis can be used with a number of substituted arylamines. p-Toluidine forms 6-methylquinoline and o-toluidine 8-methylquinoline. Both quinoline and pyridine are cyclic tertiary amines and react with acid to form salts (pyridinium and quino-linium salts) and with alkyl halides to form quaternary salts. 

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. 

The relatively vigorous reaction conditions required to effect vinyl substitution by heteroaryl halides under the influence of Pd-catalysis may lead to homo-coupling. The dominating reaction path in attempted alkenyl-ations of 4-iodopyrimidines was the formation of 4,4 -bipyrimidines (19) (Scheme 4 Section II.A.2). In reactions of 4-iodopyrimidines with a Pd-catalyst at 160°C, near-quantitative yields of the 4,4 -bipyrimidine were obtained (79CPB193). Also, in the reaction of 2-iodo-4-methylquinoline with Pd(OAc)2 as added catalyst, a major reaction path led to 4,4 -dimethyl-2,2 -biquinoline (Scheme 2 Section II.A.2.) (82CPB3647). 

The reaction of hexafluorobut-2-yne with Al,(V-dimethylbenzylamine, 8-methylquinoline, or benzo[/i]quinoline palladium dimer forms halide-bridged binuclear products with insertion of one hexafluorobut-2-yne 7.23-7.25 to the Pd-C bonds, as shown in Eqs. (7.21)-(7.23). These benzyl and quinolinyl dimeric... 

Given the abundance of aryl halides, in 2005, Pd(OAc)2-catalyzed, 8-methylquinoline- and 2-ethylpyridine-directed C(sp )-H arylation was reported by Daugulis and coworkers using low-cost aryl iodides (Scheme 1.3) [6]. An extension of P-C(sp ) arylation of carboxylic acids with aryl iodides was then achieved by Yu and coworkers (Scheme 1.2) [5]. 

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