3-(3-Nitrophenoxy)pyridine → 3-(Pyridin-3-yloxy)aniline

Participants

Reaction Steps

To a solution of 3-(3-nitrophenoxy)pyridine (4.43 g, 20.5 mmol) in EtOAc (50 mL) was added PtO2 (0.4 g) and the mixture was stirred at RT overnight under H2 (1 atm). The mixture was filtered through Celite®, the Celite® washed with EtOAc (2×20 mL) and the combined filtrates concentrated to yield (3.77 g, 99% yield) pure 3-(pyridin-3-yloxy)benzenamine as a syrup. 1H NMR (400 MHz, DMSO-d6): δ 8.34-8.32 (m, 2H), 7.40-7.39 (m, 2H), 7.02 (t, J=8.0 Hz, 1H), 6.37-6.35 (m, 1H), 6.02-6.14 (m, 2H), 5.28 (brs, 2H); MS (ESI) m/z: 187.0 (M+H+).

Provenance & Evidence