Methyl iodide → 1H-Indole, 2,3-dihydro-1-methyl-5-nitro-

Participants

Reaction Steps

To 5-nitroindoline (1.0 g, 6.1 mmol) in acetone (12 ml), powdered potassium hydroxide (1.7 g, 30.5 mmol, 5 eq) was added followed by the addition of methyl iodide (1.2 g, 9.1 mmol, 1.5 eq) at 0° C. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated and water was added and the compound was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to dryness to yield 1-methyl-5-nitro-2,3-dihydro-1H-indole (1.0 g, 92%). The crude compound was used in the next stage without purification.

Provenance & Evidence