Aniline → 2,3-Dimethylindole

Participants

Reaction Conditions

Reaction Steps

3-Butine-2-ol (0.701 g, 10 mmol), aniline (0.931 g, 10 mmol), Ru3(CO)12 (32.0 mg, 0.05 mmol) and aniline hydrochloride (0.259 g, 2.0 mmol) were placed in a 10 ml round-bottomed flask, and the mixture was stirred at 120° C. for 12 hours. After cooling, dichloromethane (3 mL) was added, and the organic layer was washed twice with 1 M hydrochloric acid (2 mL) and once with water (2 mL). The organic layer was dried over sodium sulfate, and the solvent was distilled away, whereby 2,3-dimethyl indole (1.31 g; 9.0 mmol; yield, 90%; purity, about 99%) was obtained.

Provenance & Evidence