Water → HCID 12799962, compound

Participants

Reaction Steps

A solution of phosphorus oxychloride (35 ml) in dimethylformamide (150 ml) was added to a solution of methyl 2-(n-heptyl)indole-6-carboxylate (67.5 g) in dimethylformamide (250 ml) and the resulting solution was stirred at between 70° and 85° C. for 2 hours. The mixture was then stirred for 30 minutes while the temperature dropped to 50° C. and was then poured into water (2 liters). Ice was added to reduce the temperature to 25° C. and a 50% w/v aqueous sodium hydroxide solution was added until the pH reached 11. After stirring for 10 minutes, acetic acid was added to pH 5 and the mixture was stirred until the product has solidified. Recrystallisation from methanol yielded methyl 3-formyl-2-(n-heptyl)indole-6-carboxylate (65.0 g) in the form of colourless, lustrous needles, m.p. 177°-180° C.

Provenance & Evidence