The Ruthenium Catalyzed N-Alkylation of Amides with Alcohols
- 1 September 1983
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 56 (9) , 2647-2651
- https://doi.org/10.1246/bcsj.56.2647
Abstract
Amides reacted with primary alcohols in the presence of a catalytic amount of RuCl2(PPh3)3 at 180 °C to give the corresponding N-monoalkyl amides in fairly good yields. Thus, benzamide reacted with 1-octanol to give N-octylbenzamide in 76% yield with excellent product selectivity. Little esterification of amides with alcohols occurred and selectivity to the N-alkylation was high. Most of the amides gave N-monoalkyl amides but no N,N-dialkyl amides. But formamide reacted with 1-butanol to give N,N-dibutylformamide, as well as N-butylformamide, in low yield. RuCl2(PPh3)3 was the most effective catalyst for this reaction and RuHCl(PPh3)3 also had some catalytic activity.Keywords
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