Reaction of ortho esters with secondary amines

RA Swaringen Jr, JF Eaddy…

Index: Swaringen, Roy A.; Eaddy, John F.; Henderson, Thomas R. Journal of Organic Chemistry, 1980 , vol. 45, # 20 p. 3986 - 3989

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Citation Number: 20

Abstract

The scope of the reaction of ortho esters with secondary amines has been explored. With p- toluenesulfonic acid as catalyst, N-alkylanilines and orthoformates gave high yields of N- alkylformanilides and N, N-dialkylanilines in contrast to previous work with other acid catalysts where ortho amides were produced in low yield. Aliphatic cyclic amines (eg, morpholine, piperidine) and orthoformates gave the corresponding ortho amides. This ...