Sulfuric Acid → 5-Methoxyisatin

Participants

Reaction Conditions

Reaction Steps

Concentrated sulfuric acid (45 ml) containing water (5 ml) was warmed to 60° C. and 8.6 g of N-(2-hydroximinoacetyl)-anisidine was added in one portion. The mixture was stirred at 93° C. for 10 minutes and then allowed to cool to room temperature. The mixture was poured into 500 g of ice and extracted 3 times with ethyl acetate. The combined extracts were dried over anhydrous sodium sulfate and concentrated to give 5.1 g (65% yield) of 5-methoxyisatin as a dark red solid.

Provenance & Evidence