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Report | Regular issue | Vol 12, No. 9, 1979, pp.1191-1198
Published online, 1st January, 1970
DOI: 10.3987/R-1979-09-1191
A Novel Synthetic Scheme for 2-Ethylthioisonicotinamide

Cheng-Hsia Wang,* Fang-Yu Hwang, Jhy-Ming Horng, and Chao-Tung Chen

*Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Tingchow Road, Taipei, 116, Taiwan, R.O.C.

Abstract

4-Picoline was converted to 4-cyanopyridine by ammoxidation in 98% yield. The latter was ethylated by radicals generated from silver nitrate catalyzed oxidative decarboxylation of propionic acid to form 2-ethyl-4-cyanopyridine, which was treated with ammonium sulfide to give 2-ethylthioisonicotinamide. A setup for laboratory ammoxidation was designed. Pyridine was alkylated with decarboxylating acetic, propionic, n-butanoic, isobutyric, and n-pentanoic acids to form the corresponding 2- and 4-alkylpyridines. 4-Cyanopyridine was also alkylated similarly to obtain 2-alkyl- and 2,6-dialkyl-4-cyanopyridines.