Ammonium Chloride → HCID 59426340, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-cyclobutyl-6-methoxy-2-(4-nitro-phenyl)-1H-indole (0.83 g, 2.60 mmol), iron powder (0.84 mg, 15.0 mmol), ammonium chloride (0.96 g, 18.0 mmol), and EtOH/water (25 mL/8 mL) was stirred at 80° C. for 1 h and concentrated. The residue was suspended in DMF (20 mL) and MeOH/CH2Cl2 (1:1, 20 mL). The mixture was passed through a Celite pad, washed with MeOH/CH2Cl2 (1:1), concentrated and water was added to afford a precipitate which was collected by filtration and washed with water. The solid was dissolved in CH2Cl2, dried over MgSO4, concentrated and purified on silica gel (EtOAc/hexane 20%) to provide 4-(1-cyclobutyl-6-methoxy-1H-indole-2-yl)-phenylamine (0.57 mg, 75%) as a white solid.

Provenance & Evidence