Potassium Nitrate → HCID 25139889, compound

Participants

Reaction Conditions

Reaction Steps

KNO3 (1.33 g, 13.2 mmol) was added in small portions, over 10 min, to a stirred solution of acetamide 246 (2.45 g, 12.0 mmol) in CH2SO4 (50 mL) at 0° C. and the reaction mixture was stirred at 0° C. for a further 45 min. The mixture was poured onto ice, made basic with cNH3 and extracted with DCM (3×100 mL). The solvent was evaporated to give a brown oil which was purified by chromatography on neutral Al2O3, eluting with a gradient (0-20%) of EtOAc/pet. ether, to give nitroacetamide 247 (1.49 g, 50%) as a yellow solid: mp EtOAc/pet. ether) 85-87° C.; 1H NMR δ 10.43 (br s, 1H, NH), 8.62 (s, 1H, H-7), 8.03 (s, 1H, H-4), 3.96 (s, 2H, CH2N), 3.92 (s, 2H, CH2N), 2.79 (q, J=7.2 Hz, 2H, CH2N), 2.28 (s, 3H, COCH3), 1.21 (t, J=7.2 Hz, 3H, CH3); HRMS (FAB+) calcd for C12H16N3O3 (MH+) m/z 250.1192, found 250.1195. Anal. calcd for C12H15N3O3: C, 57.8; H, 6.0; N, 16.9. Found: C, 57.9; H, 5.9; N, 16.7%.

Provenance & Evidence