Abstract

Treatment of commercially easily available quinoline, isoquinoline, benzo [f] quinoline, 5-, 6-, or 8-nitroquinoline, 2-, 4-, 6-, 7-, or 8-methylquinoline, and 6-methoxyquinoline with cyanogen bromide and sodium hydrogen carbonate in methanol affords the corresponding 1-cyano-2-methoxy-1, 2-dihydroquinolines and 2-cyano-1-methoxy-1, 2-dihydro-isoquinolines in a high yield. The yield of the objective compounds from this reaction is about twice that of the von Braun reaction not using sodium hydrogen carbonate. By the use of this reaction, synthesis of 3-bromoquinaldine, which had been difficult to synthesize heretofore, was established, and synthetic method for 3-bromo-4-(or 6-, 7-, 8-)-methylquinolines was also improved.

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