Chichibabin Reaction. II. Chichibabin Reaction of 8-Methylquinoline and Migration of the Methyl Group in the Synthesis of 3,4-Dihydro-8-methyl-carbostyril by Friedel-Crafts Reaction. : Studies on the Syntheses of Heterocyclic Compounds. CCIII.
スポンサーリンク
概要
- 論文の詳細を見る
Chichibabin reaction of 8-methylquinoline (I) in dimethylaniline with sodium amide gave a mixture of 2-amino-8-methylquinoline (II) and 2-amino-3,4-dihydro-8-methylquinoline (III), the latter of which was characterized as its hydrolyzed product, namely, 3,4-dihydro-8-methylquinolone (IV). Furthermore, Friedel-Crafts reaction of N-(o-tolyl)-β-chloropropion-amide (V) was examined in order to synthesize an authentic sample (IV) for comparison, but a mixture of 5-methyl-(VI) and 8-methyl-3,4-dihydrocarbostyril (IV) was obtained unexpectedly. This fact shows the migration of the methyl group was occurred in case of Friedel-Crafts reaction by aluminum chloride without solvent. On the other hand, catalytic hydrogenation of 8-methylcarbostyril (XI) in the presence of 40% palladium-charcoal afforded the above compound (IV), which was also identical with the sample obtained by Chichibabin reaction of I, followed by hydrolysis, and by Friedel-Crafts reaction of V.
- 公益社団法人日本薬学会の論文
- 1967-12-25
著者
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根本 英雄
Pharmaceutical Institute, Tohoku University School of Medicine
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根本 英雄
東北大薬
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亀谷 哲治
Pharmaceutical Institute Medical Faculty University Of Osaka
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