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.

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.

Citation

Potter, G. T., Jayson, G. C., Miller, G. J., & Gardiner, J. M. (2015). Amyl nitrite-mediated conversion of aromatic and heteroaromatic primary amides to carboxylic acids. Tetrahedron Letters, 56(37), 5153 - 5156. https://doi.org/10.1016/j.tetlet.2015.05.054

• Journal Article Type: Article
• Acceptance Date: May 18, 2015
• Online Publication Date: May 21, 2015
• Publication Date: Sep 9, 2015
• Publicly Available Date: May 26, 2023
• 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