Amyl nitrite-mediated conversion of aromatic and heteroaromatic primary amides to carboxylic acids. Issue 37 (9th September 2015)

• Record Type: Journal Article
• Authors: Potter, Garrett T.; Jayson, Gordon C.; Miller, Gavin J.; Gardiner, John M.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 37(2015)
• Page Start: 5153
• Page End: 5156
• Publication Date: 2015-09-09
• Subjects: Primary amide -- Carboxylic acid -- Nitration -- Diazotization; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.05.054
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: 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.