Water → HCID 59456112, compound

Participants

Reaction Conditions

Reaction Steps

1-(3-Nitrobenzenesulfonyl)-1H-indole (obtained from step (ii)) (6.62 mmol, 2.0 grams) was taken in ethanol (10 mL) in a 50 mL three-necked round-bottomed flask. Iron powder, (33.11 mmol, 1.85 grams) was added to it at 25° C. followed by addition of water (2 mL) and 1-2 drops of hydrochloric acid. The reaction mixture was then stirred for a period of 4 hours at 75-80° C. After completion of the reaction, the reaction mixture was filtered through buchner funnel and solid mass on the filter was washed twice with hot ethanol (20 mL). Combined ethanol layer was concentrated under vacuum and the residual mass was poured onto ice-cold water (30 mL) and basified with 40% sodium hydroxide solution. Aqueous layer was extracted with dichloromethane (50 mL×3). The combined dichloromethane extracts were washed with water, brine and dried over anhydrous magnesium sulfate. The volatile substances were then removed tinder reduced pressure to obtain 2.4 grams thick syrupy mass which was purified by column chromatography using neutral silicagel (100-200 mesh), eluent being ethyl acetate and n-hexane (2:3).

Provenance & Evidence