Synthesis of N??Benzylated Anilines from the Reaction of Anilines and Benzyl Chloroformate

H Pati, P Weisbruch, A Lemon, M Lee

Index: Pati, Hari; Weisbruch, Paul; Lemon, Adrienne; Lee, Moses Synthetic Communications, 2004 , vol. 34, # 5 p. 933 - 940

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Citation Number: 5

Abstract

Abstract Reactions of benzyl chloroformate with a series of substituted anilines produced N?? carbobenzyloxy “CBZ” products along with the unexpected N??benzylated “Bn” compounds. Reaction of aniline, 1a, gave the CBZ, or 2a, and Bn, or 3a, products in 29% and 14% yield, respectively. For 2??nitro??, 2??bromo??, and 2??bromo??5??nitroanilines, the N??benzylated compounds were produced exclusively. However, 2??methoxy??, 4??bromo, 4??iodo, and 4?? ...