Amination of nitrobenzene via nucleophilic aromatic substitution for hydrogen: direct formation of aromatic amide bonds

MK Stern, BK Cheng

Index: Stern, Michael K.; Cheng, Brian K. Journal of Organic Chemistry, 1993 , vol. 58, # 24 p. 6883 - 6888

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Citation Number: 45

Abstract

The first example of the direct formation of aromatic amide bonds via nucleophilic aromatic substitution for hydrogen is described. Thus, the reaction of benzamide, tetramethylammonium hydroxide dihydrate, and nitrobenzene under anaerobic conditions generates N-(4-nitropheny1)-benzamide (1)(98%) and azoxybenzene (30%) in isolated yields. In addition, other substituted benzamides and aliphatic amides are shown to ...