Dimethyl Sulfoxide → HCID 12797266, compound

Participants

Reaction Steps

Potassium hydroxide (9.0 g) was added to a solution of 2-(n-undecyl)indole-6-carboxylic acid (22.1 g) in dimethylsulphoxide (100 ml) and water (5 ml), and the mixture was stirred and warmed on a steam bath to give a suspension. After 15 minutes the suspension was removed from the steam bath, methyl iodide (15 ml) was added, and the mixture was stirred for 2 hours with occasional warming. Methyl iodide (10 ml) was added and the mixture was stirred for 1 hour. The mixture was left to cool overnight and was then poured into water and acidified with 2N hydrochloric acid. The product was collected and washed. This product was then added to a mixture of ethanol (150 ml), water (50 ml), and sodium hydroxide (6.5 g), and the mixture was heated under reflux for 1 hour and then poured into water containing acetic acid (50 ml). The product was twice recrystallised from ethanol to give 1-methyl-2-(n-undecyl)indole-6-carboxylic acid (9.6 g), in the form of a white powder, m.p. 165°-168° C.

Provenance & Evidence