Preparation of 3-methylquinoline-8-carboxylic acid

C - Chemistry – Metallurgy – 07 – D

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C07D 215/48 (2006.01)

Patent

CA 2024865

3-Methylquinoline-8-carboxylic acid I (see formula I) and derivatives thereof are prepared by reacting o-toluidine II or a derivative thereof (see formula II) with methacrolein III (see formula III) in 70-90% strength by weight sulfuric acid in the presence of iodine or of an iodine compound, and oxidizing the resulting 3,8-dimethylquinoline IV or a derivative thereof (see formula IV) with nitric acid in a solution containing sulfuric acid, in the presence of vanadium ions, by a process in which, in the sulfuric acid-containing reaction solution of the 3,8-dimethylquinoline IV, the byproducts of the reaction are first decomposed by oxidation, the resulting 3,8-dimethylquinoline solution is concentrated by distillation and the 3,8-dimethylquinoline is then oxidized in situ with nitric acid to give the 3-methylquinoline-carboxylic acid.

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