Ammonium Chloride → N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)acetamide

Participants

Reaction Steps

A solution of N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide (1.48 g, 5.40 mmol) and NH4Cl (7.22 g, 135 mmol) in MeOH (25 mL) was treated with zinc (2.82 g, 43.2 mmol) and stirred at RT for 1 h. The solids were removed via filtration through diatomaceous earth, washed with MeOH and the filtrate concentrated to near-dryness. The residue was treated with water, extracted with EtOAc (2×) and the combined organics were washed with brined, dried over Na2SO4 and concentrated to dryness. The material was treated with 60% EtOAc/Hex, the solid collected via filtration, washed with 60% EtOAc/Hex and dried to afford N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)acetamide (750 mg, 57%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.47 (s, 1H), 8.11 (d, J=5.7 Hz, 1H), 7.76 (d, J=2.9 Hz, 1H), 7.59 (d, J=2.4 Hz, 1H), 7.24 (dd, J=8.9, 3.0 Hz, 1H), 6.59 (dd, J=5.7, 2.4 Hz, 1H), 6.49 (d, J=8.9 Hz, 1H), 6.00 (s, 2H), 2.01 (s, 3H); MS (ESI) m/z: 245.1 (M+H+).

Provenance & Evidence