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Simple methodology for the aerobic N-methylation of substituted anilines catalyzed by zirconium oxychloride octahydrate, ZrOCl2·8H 2O
, Article Industrial and Engineering Chemistry Research ; Volume 52, Issue 32 , 2013 , Pages 11001-11006 ; 08885885 (ISSN) ; Rezaei Seresht, E ; Jafari, F ; Rabiei, S ; Sharif University of Technology
2013
Abstract
A highly chemoselective methodology is described for the N-methylation of functionalized anilines with dimethyl carbonate (MeOCO2Me, DMC) in the presence of ZrOCl2·8H2O. Dimethyl carbonate, which usually promotes methylation at T > 120 C and eventually under inert atmosphere, was activated in the presence of zirconium oxychloride for the desired transformation at 90 C under aerobic conditions. Aminophenols showed good reactivity in this transformation and produced the corresponding N-methylanilines, as the major products, with high selectivity. Catalyst reusability study confirmed that ZrOCl2·8H2O is a recyclable catalyst and its catalytic activity was remained unchanged at least after eight...