The Journal of organic chemistry

Mono-N-methylation of functionalized anilines with alkyl methyl carbonates over NaY faujasites. 4. Kinetics and selectivity

M Selva, P Tundo, T Foccardi

Index: Selva, Maurizio; Tundo, Pietro; Foccardi, Tommaso Journal of Organic Chemistry, 2005 , vol. 70, # 7 p. 2476 - 2485

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Citation Number: 45

Abstract

In the presence of NaY faujasite as the catalyst, the reaction of bifunctional anilines (1-4: XC6H4NH2; X= OH, CO2H, CH2OH, and CONH2) with methyl alkyl carbonates [MeOCO2R': R'= Me or MeO (CH2) 2O (CH2) 2] proceeds with a very high mono-N-methyl selectivity (XC6H4NHMe up to 99%), and chemoselectivity as well, with other nucleophilic functions (OH, CO2H, CH2OH, CONH2) fully preserved from alkylation and/or transesterification ...