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■ Reinvestigation of the Reaction of Nicotinic Acid 1-Oxide with Acetic Anhydride

Hiroyuki Nagano, Masatomo Hamana, Yoshiharu Nawata, Supaluk Prachayasittikul, Ashraf N. Abdel-Sayed, and Ludwing Bayer

*Central Research Laboratories, Chugai Pharmaceutical Company, Ltd., Takada 3-41-8, Toshima-ku, Tokyo 171, Japan

Abstract

Reinvestigation of the reaction of nicotinic acid 1-oxide (1) with boiling acetic anhydride has revealed that the primary product is not 2-acetylnicotinic acid 1-oxide (3) but 3- acetoxy-4-aza-3-methyl-1(3H)-isobenzofuranone 4-oxide (2), the acetate of the ring tautomer of 3. Reactions of 2 and 3 with phosphorus trichloride and some related reactions are reported.