Water → 1-Methyl-6-nitro-1H-indole

Participants

Reaction Steps

To a slurry of 0.33 g (8.3 mmol) of NaH (60% dispersion in oil) in 30 ml of dried dimethylformamide ("DMF"), was added 0.973 g (6.00 mmol) of commercially available (Lancaster, Windham, N.H.) 6-nitro-IH-indole (1) at 0-5° C. over a period of 10 minutes. After 1 hour stirring at the same temperature, 0.75 ml (12.1 mmol) of methyl iodide was added and the mixture was stirred at the same temperature for 30 minutes, then at room temperature for 1 hour, poured into ice and water and extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4, and concentrated to yield 0.814 g (77.5%) of 1-methyl-6-nitro-1H-indole (2) as a yellow solid. This material was used without purification.

Provenance & Evidence