Studies on Tertiary Amine Oxides. LXIV. Reaction of 4-Nitroquinoline 1-Oxide and Related Compounds with Potassium Cyanide

Treatment of 4-nitroquinoline 1-oxide (1) with potassium cyanate in hot ethanol afforded 4-ethoxyquinoline 1-oxide. On the other hand when potassium cyanide was applied instead of the cyanate, the reaction followed an alternate course giving 3-cyano-4-quinolinol (3). Compound 3 was produced also from reactions in 90% ethanol, DMF, DMSO and dioxane, the best yield being obtained from the reactions in DMF at 80-90°. It was further disclosed that besides 1, 2-chloro-(13), 2-bromo-4-nitroquinoline 1-oxides (14), 4-nitroquinoline (18) and 2-bromo-4-nitroquinoline (19) underwent the same type of reaction.