Studies on Organic Fluorine Compounds. VI. Preparations and Reactions of (Trifluoromethyl) quinoline N-Oxides

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Abstract
First, 2-, 3-, and 4-(trifluoromethyl) quinoline 1-oxides (IV, V, and VI) were synthesized. Next, their reactions with acetic anhydride and phosphoryl chloride and the Reissert reaction were carried out and compared with the reactions in the cases of pyridine series. The reactions of IV with acetic anhydride and phosphoryl chloride gave 4-substituted products, whereas in the cases of V and VI 2-substituted products were obtained. In the Reissert reaction of IV, the starting material was recovered ; in the cases of V and VI, 2-nitrile derivative was produced as well as a considerable amount of 2-hydroxy derivative as by-product. Then, the reaction of V with only potassium cyanide in methanol was carried out to obtain 3-(trifluoromethyl) cinchoninonitrile. The unique result as above was concluded to be due to the naphthoid structure of quinoline.

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