A Highly Efficient Copper-Catalyzed Method for the Synthesis of 2-Hydroxybenzamides in Water

Shah Jaimin Balkrishna; Sangit Kumar

doi:10.1055/s-0031-1289755

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(9): 1417-1426
DOI: 10.1055/s-0031-1289755

paper

A Highly Efficient Copper-Catalyzed Method for the Synthesis of 2-Hydroxybenzamides in Water

Shah Jaimin Balkrishna

Department of Chemistry, Indian Institute of Science Education and Research (IISER), Bhopal 462023, MP, India , Fax: +91(755)409 2392 eMail: SangitKumar@iiserbhopal.ac.in

,

Sangit Kumar*

Department of Chemistry, Indian Institute of Science Education and Research (IISER), Bhopal 462023, MP, India , Fax: +91(755)409 2392 eMail: SangitKumar@iiserbhopal.ac.in

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Abstract

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Abstract

An efficient copper-catalyzed synthetic method for the preparation of 2-hydroxybenzamides is described for the first time from 2-chlorobenzamide substrates using copper iodide/1,10-phenanthroline and a base, potassium hydroxide, in neat water. By using this reaction, a series of 2-hydroxybenzamides with functional groups such as fluoro, chloro, iodo, methoxy, amide, and alcohol have been obtained in 33–96% yield. Other aromatic 2-chloroarylamides such as naphthalene, pyridine, and thiophene are found to be equally compatible to the reaction. It is proposed that the reaction proceed via formation of copper-amide complex, which may facilitate the hydroxylation in water. Overall, the first report on copper-catalyzed hydroxylation reaction in water and first catalytic route for the synthesis of 2-hydroxybenzamides is presented. Simple purification procedure and convenience of employing low-cost reagents in neat water make this method practical and economical for the synthesis of 2-hydroxybenzamides.

Key words

copper - 2-hydroxybenzamides - hydroxylation - catalysis in water - C–O coupling

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