Selective N‐Monomethylation of Anilines with Methanol Catalyzed by Commercial Pd/C as an Efficient and Reusable Catalyst

Abstract

AbstractN‐methylation of amines is one of the most important C−N bond‐forming reactions and is widely utilized for the synthesis of numerous agrochemicals, drugs, natural products, and dyes. In this paper, the N‐monomethylation of aniline derivatives using Pd/C catalyst and methanol as the methylation reagent was investigated. The N‐monomethylation of various anilines was achieved with high activity and selectivity under relatively mild reaction conditions, and the yield of N‐monomethyl anilines was over 90 %. Notably, the commercial, readily available, and inexpensive heterogeneous catalyst, Pd/C, could be easily recovered and reused more than five times with only a slight decrease in activity; gram‐scale experiments were also successfully performed.