Sodium Nitrate → 2-(4-Hydroxy-3,5-dimethylphenyl)-3-methyl-5-nitroindole

Participants

Reaction Conditions

Reaction Steps

5.0 g of 2-(4-hydroxy-3,5-dimethylphenyl)-3-methylindole was added to 100 ml of concentrated sulfuric acid, and the mixture was stirred at 0° C. Then, a solution of 1.76 g of sodium nitrate in 50 ml of concentrated sulfuric acid was added dropwise, and the mixture was stirred for 15 minutes. The reaction mixture was poured into ice-water, and extracted with ether. The resulting crude product was purified by silica gel column chromatography. Recrystallization from ether-hexane gave 2-(4-hydroxy-3,5-dimethylphenyl)-3-methyl-5-nitroindole.

Provenance & Evidence