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

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概要

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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.

• 公益社団法人日本薬学会の論文
• 1970-10-25

著者

• 伊藤 義雄

  Faculty Of Pharmaceutical Science Meijo University

• 広田 穣

  (present Address):dept. Of Applied Chemistry Faculty Of Engineering National Yokohama University

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• Theoretical Considerations on the Nitration of 2-Anilinopyridine
• Syntheses of Nitrogen-containing Heterocyclic Compounds. XIX. Nitration of 2-Anilinopyridine
• Quinoline Derivatives. XIV. Chemistry of 2-(Phenylamino)-lepidine Derivatives
• Quinoline Derivatives. XVI. Nitration of 2-Anilino-4-methylquinoline with the Mixed Acid of Nitric and Sulfuric Acid

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