Hydrochloric Acid → 2-(6,7-Dichloroisatin-1-yl)acetic acid

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Reaction Steps

A solution of 5,6-dichloroisatin (1.0 g, 4.65 mmol) in DMF (20 ml) was cooled in an ice-bath. Sodium hydride (5.11 mmol, 0.20 g 60% dispersion in mineral oil) was added and the mixture was stirred for 20 min. Ethyl 2-bromoacetate (0.37 ml, 5.11 mmol) was added and stirring was continued for 2 hours. The resulting mixture was poured into diluted hydrochloric acid (200 ml, 4M), heated to reflux for 2 hours, filtered, cooled and extracted with ethyl acetate. The organic extract was dried over magnesium sulphate and evaporated to dryness to leave the desired product (0.85 g, 67%).

Provenance & Evidence