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Monoalkylation of Primary Amines and N-Sulfinylamides Using Raney-Nickel
J. L. Garcia Ruano*, A. Parra, J. Alemán, F. Yuste, V. M. Mastranzo
Universidad Autónoma de Madrid, Spain and Universidad Nacional Autónoma de México, Coyoacán, México
23 March 2009 (online)
An efficient monoalkylation method of primary amines using Raney-nickel (Ra-Ni) was developed. Thus, the monoalkylation of aniline (0.2 mmol) was carried out with ethanol in the presence of Ra-Ni to give N-ethylaniline (2a) in 83% yield. The Ra-Ni was recovered by simple filtration and reused four times without any loss of catalytic activity (average: 81% yield). The mono-alkylation of several primary amines was also examined under similar reaction conditions to give the corresponding monoalkylated amines 2b-e in 79-86% yield.