Ethanol → Methyl indole-6-carboxylate

Participants

Reaction Steps

Sodium dithionate (164.4 g; 16 equiv.) was added over a period of 20 minutes to a solution of 4-(2-(dimethylamino)vinyl)-3-nitrobenzoic acid (14 g; 1 equiv.) in a mixture of THF (42 ml), ethanol (42 ml) and water (140 ml). The reaction mixture was heated for 90 min. at reflux and then stirred for 12 hours at room temperature. When the conversion was complete, dichloromethane was added, the phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate. After removal of the solvent under reduced pressure, purification was carried out by column chromatography (silica gel, 10% ethyl acetate/hexane). Methyl 1H-indole-6-carboxylate (8 g; 40%) was obtained in the form of a solid.

Provenance & Evidence