Methanol → 2-fluoro-N1-(3-(tetrahydrofuran-2-yl)propyl)benzene-1,4-diamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-fluoro-4-nitro-N-(3-(tetrahydrofuran-2-yl)propyl)aniline (480 mg, 1.79 mmol), MeOH (40 mL), water (20 mL), iron powder (504 mg, 9.03 mmol) and NH4Cl (193 mg, 3.61 mmol) was stirred at 60° C. overnight. The mixture was then cooled to rt and saturated NaHCO3 aqueous solution was added. The resulting mixture was filtered and the filtrate was extracted with DCM (30 mL×4). The combined organic layers were washed with brine (40 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as red liquid (260 mg, 61%).

Provenance & Evidence