第3級アミンオキシドに関する研究(第32報) : 2-Halogeno-4-nitroquinoline 1-Oxidesの合成とそのアシル化剤との反応について

概要

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Nitration of 2-chloro-and 2-bromo-quinoline 1-oxides with 80% sulfuric acid-potassium nitrate results in formation of 2-chloro-and 2-bromo-4-nitroquinoline 1-oxides (I and II) in a good yield but the use of 95% sulfuric acid was found to drastically reduce the yield. Reaction of I and II with some acylation agents was examined. Reaction of I with phosphorus tribromide and that of II with phosphorus trichloride in the cold respectively afforded II and I. Reaction of I with acetyl chloride and with benzoyl chloride afforded 1-acetoxy-(III) and 1-benzoyloxy-carbostyril (V), while the reaction of I or II with acetic anhydride-potassium acetate gave 4-nitrocarbostyril 1-oxide (VII). Since the reaction of 2,4-dichloroquinoline 1-oxide (VI) and benzyl chloride-silver nitrite resulted in the formation of V, formation of III and V passed through the formation of VI from I, and the acyl nitrite formed as a by-product of VI reacts further to produce III and V.
公益社団法人日本薬学会の論文
1968-06-25