Sulfuric Acid → Indole

Participants

Reaction Conditions

Reaction Steps

2-(5-Fluoro-6-methoxy-1H-indol-3-yl)ethanol (Ind-26) A solution of dihydrofuran (242 mg, 3.46 mmol) in acetonitrile (10 ml) was added dropwise to a solution of (4-fluoro-3-methoxyphenyl)hydrazine hydrochloride [1.00 g, 3.46 mmol (based on a purity of the educt of 68%)] in acetonitrile (30 ml) and 4% aqueous sulfuric acid (30 ml) at room temperature. Thereafter, the temperature was increased to 80° C. and the reaction mixture was stirred at this temperature for 2 h and then cooled to room temperature and the solvent was removed i. vac. 5% sodium bicarbonate solution was added to the residue and the mixture was extracted with ethyl acetate (3×50 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac.

Provenance & Evidence