3-Chloro-5-(3-nitrophenoxy)pyridine → 3-(5-Chloropyridin-3-yloxy)benzenamine

Participants

Reaction Steps

To a solution of 3-chloro-5-(3-nitrophenoxy)pyridine (0.2 g, 0.8 mmol) in EtOAc (10 mL) was added PtO2 (0.02 g) and the mixture was stirred for 4 h under H2 (1 atm). It was then filtered through a Celite® pad and washed with EtOAc (2×5 mL). The combined organic extracts were concentrated to afford 3-(5-chloropyridin-3-yloxy)benzenamine (0.165 g, 93% yield) which was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.39 (d, J=2.0 Hz, 1H), 8.31 (d, J=2.8 Hz, 1H), 7.54-7.53 (m, 1H), 7.05 (t, J=8.0 Hz, 1H), 6.42-6.39 (m, 1H), 6.25-6.19 (m, 2H), 5.33 (brs, 2H); MS (ESI) m/z: 221.0 (M+H+).

Provenance & Evidence