Hydroxylamine → N'-hydroxy-4-pyridin-3-yloxybenzenecarboximidamide

Participants

Reaction Steps

4-(Pyridin-3-yloxy)benzonitrile (486 mg, 2.48 mmol) was dissolved in ethanol (10.0 mL) then hydroxylamine (1.0 mL, 9.9 mmol) was added and the mixture was refluxed for 4 hours. The reaction was cooled to room temperature and concentrated in vacuo to give the product which immediately formed yellow solid (565 mg, 100%) which was taken to the next step without further purification. 1H NMR (500 MHz, DMSO-d6) δ(ppm): 5.83 (2H, bs), 7.05 (2H, d, J=9.0 Hz), 7.43 (1H, ddd, J=8.4, 4.4, 0.8 Hz), 7.46 (1H, ddd, J=8.4, 2.7, 1.6 Hz), 7.72 (2H, d, J=8.8 Hz), 8.39 (1H, dd, J=4.5, 1.5 Hz), 8.41 (1H, d, J=2.8 Hz), 9.64 (1H, bs). 13C NMR (125 MHz, DMSO-d6) δ(ppm): 118.1 (CH), 124.8 (CH), 126.1 (CH), 127.4 (CH), 129.2, 134.5 (CH), 141.2 (CH), 144.9 (CH), 150.3, 153.0, 156.7. MS (FAB+): 230 (MH+). HRMS for C12H11N3O2 (MH+): calculated: 230.0930; found 230.0941.

Provenance & Evidence