Synthesis

Efficient conversions of Carboxylic acids into O-alkyl, N-alkyl and O, N-dialkylhydroxamic acids

AR Katritzky, N Kirichenko, BV Rogovoy

Index: Katritzky, Alan R.; Kirichenko, Nataliya; Rogovoy, Boris V. Synthesis, 2003 , # 18 p. 2777 - 2780

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Citation Number: 17

Abstract

The acylbenzotriazoles 2a-d were conveniently prepared from carboxylic acids by reaction with 1-methanesulfonyl-1H-benzotriazole as reported previously. [30] Reaction of 1-benzoyl-1H-benzotriazole (2a) with hydroxylamine hydrochloride in the presence of potassium tert-butoxide in THF at 20 °C gave the desired hydroxamic acid 3a in only 17% yield with benzotriazole and benzoic acid as by-products. Similar reaction with O-ethylhydroxylamine gave the corresponding O- ...