Ammonia → 2-(1-methyl-1H-indol-3-yl)ethan-1-ol

Participants

Reaction Steps

To a solution of sodium amide from 0.63 g sodium in 50 ml liquid ammonia is added in dropwise fashion a solution of 3.22 g of 3-(2-hydroxyethyl)indole in 10 ml diethyl ether. After stirring 10 minutes a solution of 1.37 ml methyl iodide in 1.5 ml diethyl ether is added in one portion. The mixture is stirred for 15 minutes and then the ammonia is allowed to evaporate. The residue is mixed with 100 ml water and is extracted into 200 ml diethyl ether. The organic phase is separated and is dried over magnesium sulfate. Filtration and evaporation affords 3.64 g of 1-methyl-3-(2-hydroxyethyl)indole, an oil.

Provenance & Evidence