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

TETRAHEDRON LETTERS

卷:56

Article

Potter, Garrett T.¹  Jayson, Gordon C.²  Miller, Gavin J.³  Gardiner, John M.¹ 

[1] Univ Manchester, Fac EPS, Sch Chem, Manchester Inst Biotechnol, Manchester M1 7DN, Lancs, England

[2] Univ Manchester, Inst Canc Sci, Manchester M20 4BX, Lancs, England

[3] Univ Manchester, Sch Chem, Fac EPS, Manchester M13 9PL, Lancs, England

关键词: Primary amide;    Carboxylic acid;    Nitration;    Diazotization;   

DOI  :  10.1016/j.tetlet.2015.05.054

来源: Elsevier

【 摘 要 】

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. (C) 2015 Published by Elsevier Ltd.

【 授权许可】

Free