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
Full Text: HTML
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 ...
Related Articles:
Fast deprotection of phenoxy benzyl ethers in transfer hydrogenation assisted by microwave
[Quai, Monica; Repetto, Claudio; Barbaglia, Walter; Cereda, Enzo Tetrahedron Letters, 2007 , vol. 48, # 7 p. 1241 - 1245]
The Reduction of p-Hydroxyformanilide by Lithium Aluminum Hydride to N-Methyl-p-aminophenol
[Ehrlich Journal of the American Chemical Society, 1948 , vol. 70, p. 2286]
[Dhakshinamoorthy, Amarajothi; Sharmila, Alagarsamy; Pitchumani, Kasi Chemistry - A European Journal, 2010 , vol. 16, # 4 p. 1128 - 1132]