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Making Amides from Nitriles

The hydrolysis of nitriles is a satisfactory method for preparation of unsubstituted amides and is particularly convenient when hydrolysis is induced under mildly basic conditions by hydrogen peroxide:

For the preparation of amides of the type \(\ce{R_3CNHCOR}\), which have a tertiary alkyl group bonded to nitrogen, the Ritter reaction of an alcohol or alkene with a nitrile or hydrogen cyanide is highly advantageous. This reaction involves formation of a carbocation by action of strong sulfuric acid on an alkene or an alcohol (Equation 1), combination of the carbocation with the unshared electrons on nitrogen of \(\ce{RCN}\) (Equation 2), and then addition of water (Equation 3). We use here the preparation of an \(\ce{N}\)-tert-butylalkanamide as an example; \(\ce{RC \equiv N}\) can be an alkyl cyanide such as ethanenitrile or hydrogen cyanide itself:

\(\tag{1}\)

\(\tag{2}\)

\(\tag{3}\)

This reaction also is useful for the preparation of primary amines by hydrolysis of the amide. It is one of the relatively few practical methods for synthesizing amines with a tertiary alkyl group on the nitrogen:

Contributors

  • John D. Robert and Marjorie C. Caserio (1977) Basic Principles of Organic Chemistry, second edition. W. A. Benjamin, Inc. , Menlo Park, CA. ISBN 0-8053-8329-8. This content is copyrighted under the following conditions, "You are granted permission for individual, educational, research and non-commercial reproduction, distribution, display and performance of this work in any format."