Hydrazine hydrate (1:1) → HCID 68667054, compound

Participants

Reaction Steps

A solution of methyl 4-[(2-nitrophenyl)amino]benzoate (20 g, 48 mmol) in methanol under nitrogen was treated with 5% Pd/C (1.8 g, 30 w/v) and hydrazine hydrate (11.7 g, 230 mmol), heated at reflux temperature for 2 h, cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The resultant residue was partitioned between CH2Cl2 and water. The organic phase was separated, dried over Na2SO4 and concentrated under vacuum. The resultant residue was purified with flash column chromatography with (silica, EtOAc:hexanes 4:6) to give 4-(2-aminophenylamino)benzoic acid methyl ester in 80% yield, 1H NMR (400 MHz, CDCl3): 7.87 (d, J=8.8 Hz, 2H), 7.13 (d, J=8.0 Hz, 1H) 7.09 (t, J=8 Hz, 1H), 6.82 (d, J=8.0 Hz, 1H), 6.78 (t, J=8 Hz, 1H), 6.67 (d, J=8.0 Hz, 2H), 5.4 (bs, 1H), 3.8 (s, 3H), 3.71 (s, 2H); LCMS (ESI+) 243 (MH+).

Provenance & Evidence