Tetrahedron

Highly specific N-monomethylation of primary aromatic amines

A Le Pera, A Leggio, A Liguori

Index: Le Pera, Adolfo; Leggio, Antonella; Liguori, Angelo Tetrahedron, 2006 , vol. 62, # 25 p. 6100 - 6106

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Citation Number: 11

Abstract

A synthetic methodology for the specific conversion of primary aromatic amines into their N- monomethyl derivatives under very mild conditions is presented. Anilines are treated with 4- nitrobenzenesulfonyl (nosyl) chloride to generate the corresponding sulfonamides 2 in high yields. The subsequent N-methylation reaction of the sulfonamides 2 with a solution of diazomethane is rapid and quantitative. Removal of the nosyl protecting group is readily ...