Methane → HCID 12799945, compound

Participants

Reaction Conditions

Reaction Steps

Phosphorus oxychloride (27.5 ml) was added dropwise during 20 minutes to stirred N,N-dimethyldodecanamide (84.9 g) at room temperature. The temperature of the mixture rose during the addition to 50° C. The mixture was stirred and heated at 90° C. for 15 minutes and then methyl indole-6-carboxylate (33.4 g) was added portionwise to the stirred mixture during 10 minutes, the temperature of the mixture being maintained at 90° C. during the addition. The mixture was then stirred for 2 hours at 90° C. and was then poured onto ice. The aqueous mixture was extracted with chloroform (3×300 ml) and the extract was dried over magnesium sulphate and was evaporated to give a red brown oil. The oil was dissolved in boiling methanol (100 ml), the solution was treated with charcoal and the solution was filtered and cooled (0° C.) to give methyl 3-(n-dodecanoyl)indole-6-carboxylate (26.7 g), in the form of a buff solid, m.p. 167°-169° C.

Provenance & Evidence