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Issue 10, 1976
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Anodic oxidation of carboxamides. Part II. Anodic oxidation and pyridination of N-methyl-4′-methoxybenzanilide in acetonitrile

Abstract

Anodic oxidation of N-methyl-4′-methoxybenzanilide (N-methyl-MBA) was investigated by cyclic voltammetry end controlled potential electrolysis at a glassy-carbon electrode in acetonitrile- in the presence and absence of water or pyridine. In acetonitrile N-methyl-MBA showed a single anodic peak at 1.27 V versus the saturated calomel electrode with a peak height corresponding to that of a two-electron process. Added pyridine and/or water had no effect on the peak potential or peak height. On electrolysis of N-methyl-MBA in acetonitrile, p-benzoquinone, and N-methylbenzamide were mainly formed. Essentially the same results were obtained on electrolysis in the presence of added water. In the presence of excess of pyridine, electrolysis of N-methyl-MBA resulted in the formation of pyridinated N-methyl-MBA in which the pyridinium group was meta to the anilide nitrogen atom on the N-methylanisidine ring. The results were compared with those obtained on anodic oxidation of 4′-methoxybenzanilide.

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Article information


J. Chem. Soc., Perkin Trans. 2, 1976, 1180-1183
Article type
Paper

Anodic oxidation of carboxamides. Part II. Anodic oxidation and pyridination of N-methyl-4′-methoxybenzanilide in acetonitrile

M. Masui, H. Ohmori, H. Sayo, A. Ueda and C. Ueda, J. Chem. Soc., Perkin Trans. 2, 1976, 1180
DOI: 10.1039/P29760001180

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