Iodine → 3-iodo-5,6-dimethoxy-1-methyl-1H-indole

Participants

Reaction Conditions

Reaction Steps

0.465 g of powdered potassium hydroxide is added to a solution of 0.5 g of 5,6-dimethoxy-1H-indole in 15 ml of dimethylformamide. A solution of 0.725 g of bisublimated iodine in 15 ml of dimethylformamide is added dropwise to the above mixture. After agitation of the reaction medium for approximately 3 hours at a temperature in the region of 20° C., 0.21 ml of iodomethane is added dropwise, maintaining the mixture at this same temperature by cooling using a water bath. After agitation at around 20° C. for 1 hour 30 minutes, the mixture is run into a solution of 1.5 g of sodium thiosulfate in 150 ml of water cooled to around 5° C., and agitated for approximately 10 minutes. The precipitate is filter-dried, washed with five times 5 ml of water cooled to around 5° C., and then dried under vacuum (13 kPa) over phosphorus pentaoxide. 0.78 g of 3-iodo-5,6-dimethoxy-1-methyl-1H-indole is obtained in the form of a solid, the characteristics of which are as follows:

Provenance & Evidence