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Amyl nitrite-mediated conversion of aromatic and heteroaromatic primary amides to carboxylic acids

Potter, Garrett T.; Jayson, Gordon C.; Miller, Gavin J.; Gardiner, John M.

Amyl nitrite-mediated conversion of aromatic and heteroaromatic primary amides to carboxylic acids Thumbnail


Authors

Garrett T. Potter

Gordon C. Jayson

John M. Gardiner



Abstract

A series of aromatic and heteroaromatic primary amides were converted directly to carboxylic acids by heating with amyl nitrite in acetic acid. Most conversions proceeded to give reasonable to excellent yields on a range of substrates containing various functional groups. This reagent system is thus applicable for the direct hydrolysis of a range of different primary carboxamides. The reaction with a phenolic aromatic substrate afforded two alternative nitration products as major outcomes, evidencing alternative reaction pathways resulting from the free phenolic OH.

Journal Article Type Article
Acceptance Date May 18, 2015
Online Publication Date May 21, 2015
Publication Date Sep 9, 2015
Publicly Available Date Mar 29, 2024
Journal Tetrahedron Letters
Print ISSN 0040-4039
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 56
Issue 37
Pages 5153 - 5156
DOI https://doi.org/10.1016/j.tetlet.2015.05.054
Keywords Primary amide, Carboxylic acid, Nitration, Diazotization
Publisher URL https://doi.org/10.1016/j.tetlet.2015.05.054

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