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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 6
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Original Articles

Synthesis of Hydroxamic Acids by Activation of Carboxylic Acids with N,N′-Carbonyldiimidazole: Exploring the Efficiency of the Method

, , &
Pages 927-935 | Received 07 Apr 2009, Published online: 22 Feb 2010
 

Abstract

Activation of carboxylic acids with N,N′-carbonyldiimidazole followed by the reaction with anhydrous or aqueous hydroxylamine hydrochloride was demonstrated to be an operationally simple method for the synthesis of hydroxamic acids in good yield and high purity after aqueous workup. The potential by-product, N,O-diacylhydroxylamine, is cleanly transformed to hydroxamic acid in these reaction conditions.

ACKNOWLEDGMENT

Partial financial support from the European Regional Development Fund (VPD1/ERAF/CFLA/05/APK/2.5.1/000029/014) is gratefully acknowledged.

Notes

a Method A: addition of solid NH2OH·HCl; method B: addition of aqueous 2 M NH2OH·HCl (2 eq) after activation of carboxylic acid.

b Crystallized from water.

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