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Synthesis of N-methoxy-N-methylaminocarbonyl-l, 4-benzoquinone: the First Quinone Carrying an N-methoxy-N-methylamino Group

Ahmad, Faujan (1988) Synthesis of N-methoxy-N-methylaminocarbonyl-l, 4-benzoquinone: the First Quinone Carrying an N-methoxy-N-methylamino Group. Pertanika, 11 (1). pp. 87-90.

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Abstract

We report herein a four-step preparation of the title compound. Gentisic acid (1) was firstly converted into its diacetate (2) by treatment with acetic anhydride in the presence of concentrated sulfuric acid. Treatment of the diacetate with oxalyl chloride in dichloromethane in the presence of dimethylformamide followed by N-D-dimethyl-hydroxyamine hydrochloride and pyridine gave 2, 5-diacetoxy-Nmethoxy- N-methylbenzamide (3). Reaction of this with sodium hydrogen carbonate to generate the hydroquinone (4) followed by oxidation with silver oxide gave the desired quinone (5).

Item Type:Article
Keyword:Quinone synthesis N-methoxy-N-methylaminocarbonyl-l, 4-benzoquinone
Faculty or Institute:Faculty of Environmental Studies
ID Code:2698
Deposited By: Nur Izyan Mohd Zaki
Deposited On:17 Nov 2009 01:55
Last Modified:27 May 2013 07:02

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