Water → HCID 12799960, compound

Participants

Reaction Steps

A solution of phosphorus oxychloride (20 ml) in dimethylformamide (80 ml) was added to a solution of methyl 2-(n-undecyl)indole-6-carboxylate (58.3 g) in dimethylformamide (250 ml) and the mixture was stirred at a temperature of 55°-90° C. for 2 hours. After cooling, the mixture was poured into rapidly stirred water. Aqueous sodium hydroxide (50% w/v) was added until pH 12, the mixture was stirred for 10 minutes, and then glacial acetic acid was added to pH 5. The mixture was stirred until the gummy product solidified. The solid was then collected and recrystallised from ethanol to give methyl 3-formyl-2-(n-undecyl)indole-6-carboxylate (52.5 g), in the form of a buff powder, m.p. 147°-149° C.

Provenance & Evidence