Water → HCID 67254243, compound

Participants

Reaction Steps

Iron powder (6.3 g, 112 mmol) was added to a mixture of 3-(5-chloro-pyridin-3-yloxy)-5-nitro-benzonitrile (3.1 g, 11.2 mol) in acetic acid (100 mL) and the reaction was stirred at RT for 6 h. Water (200 mL) was added and the mixture was neutralized to pH 7 with saturated Na2CO3 solution and was extracted with EtOAc (3×150 mL). The combined organics were washed with brine, dried (Na2SO4), concentrated in vacuo and purified on silica gel to give 3-amino-5-(5-chloropyridin-3-yloxy)benzonitrile (1.92 g, 71% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.53 (d, J=1.6 Hz, 1H), 8.44 (d, J=2.4 Hz, 1H), 7.80 (t, J=2.4 Hz, 1H), 6.77 (s, 1H), 6.72 (d, J=1.6 Hz, 1H), 6.56 (d, J=2.0 Hz, 1H), 5.92 (s, 2H); MS (ESI) m/z: 246.2 [M+H]+.

Provenance & Evidence