7-Nitroindole → 3-chloro-7-nitro-1H-indole

Participants

Reaction Steps

1.076 g (6.64 mmol) of 7-nitro-1H-indole was dissolved in 30 ml of acetonitrile, and 920 mg (6.89 mmol) of N-chlorosuccinimide was added thereto. After stirring at room temperature for 36 hours, an aqueous saturated sodium bicarbonate was added thereto. The precipitates were collected by filtration and washed with water, to give 1.2 g of 3-chloro-7-nitro-1H-indole. 863 mg (4.39 mmol) of the powder was suspended in 10 ml of ethanol, and 4.95 g (21.9 mmol) of stannous chloride.dihydrate and 100 μl of concentrated hydrochloric acid were added thereto. After heating under reflux for 30 minutes, an aqueous saturated sodium bicarbonate was added thereto and the insoluble matters were filtered off. After extracting by adding ethyl acetate thereto, the extract was dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography, to give 490 mg of the title compound.

Provenance & Evidence