Ammonium Chloride → 1-N-Benzyl-5-fluorobenzene-1,2-diamine

Participants

Reaction Conditions

Reaction Steps

A mixture of benzyl-(5-fluoro-2-nitrophenyl)amine (3.8 g, 15.2 mmol), iron powder (3.42 g, 60.8 mmol) and ammonium chloride (4.7 g, 91.2 mmol) in methanol (40 mL) and water (10 mL) was heated to 90° C. for 2 h, under an atmosphere of nitrogen. The resultant mixture was diluted with methanol (20 mL) and filtered through Celite®. The Celite® was washed with DCM, methanol and EtOAc (4×) and the filtrate concentrated in vacuo. The residue was partitioned between water (25 mL) and EtOAc (40 mL) and the aqueous layer was extracted with EtOAc (2×30 mL). The combined organic fractions were washed with brine (25 mL), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a dark brown gum (2.17 g, 66%). The crude material was used without purification in the next step. 1H NMR (CDCl3, 400 MHz): δ 7.41-7.25 (5H, m), 6.67-6.59 (1H, m), 6.40-6.28 (2H, m), 4.28 (2H, s)

Provenance & Evidence