Ritter Reaction

The acid-induced nucleophilic addition of a nitrile to a carbenium ion, followed by hydrolysis to the corresponding amide.

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Mechanism of the Ritter Reaction

Any substrate capable of generating a stable carbenium ion is a suitable starting material; primary alcohols do not react under these conditions, with exception of benzylic alcohols:

The carbenium ion adds to the nitrile nitrogen to give a nitrilium ion intermediate, which undergoes hydrolysis to the corresponding amide upon aqueous work-up.

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Recent Literature

An efficient method for the conversion of aromatic and aliphatic nitriles to the corresponding N-tert-butyl amides: a modified Ritter reaction
K. L. Reddy, Tetrahedron Lett., 2003, 44, 1453-1455

Synthesis of N-Benzhydrylamides from Nitriles by Ritter Reactions in Formic Acid
G. C. Gullickson, D. E. Lewis, Synthesis, 2003, 681-684.

A CAN-Induced Cyclodimerization-Ritter Trapping Strategy for the One-Pot Synthesis of 1-Amino-4-aryltetralins from Styrenes
V. Nair, R. Rajan, N. P. Rath, Org. Lett., 2002, 4, 1575-1577.