Quinoline Derivatives. XVI. Nitration of 2-Anilino-4-methylquinoline with the Mixed Acid of Nitric and Sulfuric Acid

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Nitration of 2-anilino-4-methylquinoline (I) with mixed acids gives different products according to the concentration of sulfuric acid used. In 50% sulfuric acid solution, 2- (o-nitroanilino) -4-methylquinoline (II) and 2- (p-nitroanilino) -4-methylquinoline (IV) are formed in approximately equal quantity, while in 85% sulfuric acid solution, IV and 2- (p-nitroanilino) -4-methyl-6-nitroquinoline (V) are mainly formed. In 95% sulfuric acid, V and a small amount of 2- (2', 4'-dinitroanilino) -4-methyl-6-nitroquinoline (VI) are formed. On the other hand, nitration of I with acetyl nitrate results in the characteristic formation of II and 2- (2', 4'-dinitroanilino) -4-methylquinoline (III). It is certain, therefore, that nitration of I with nitric acid in 95% sulfuric acid and that with acetyl nitrate have a different reaction mechanism ; the former reaction proceeding in [chemical formula] type and the latter in [chemical formula] type.

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