Ammonium Chloride → 4-(3-Chlorophenoxy)-2-methylaniline

Participants

Reaction Steps

To a stirred solution of 4-(3-chloro-phenoxy)-2-methyl-1-nitro-benzene (0.56 g, 2.12 mmol) in ethanol and water, iron (594 mg, 10.6 mmol) and saturated ammonium chloride (569 mg, 10.6 mmol) were added. This reaction mixture was then heated to reflux for 12 h. This was then filtered through celite and then extracted with EtOAc (3×15 mL). The EtOAc layer was washed with brine, dried over sodium sulfate and concentrated. This was then purified by chromatography (11% EtOAc in hexanes) to afford 4-(3-chloro-phenoxy)-2-methyl-phenylamine (0.43 g, 87%). MS (M+H)+=234.1; 1H NMR (CDCl3) δ: 7.17 (t, J=6.0 Hz, 1H), 6.95 (d, J=2.8 Hz, 1H), 6.88-6.86 (m, 1H), 6.82-6.71 (m, 2H), 6.65 (d, J=6.27 Hz, 1H).

Provenance & Evidence