Sodium Bicarbonate → HCID 11381836, compound

Participants

Reaction Steps

A stirred mixture of 6-propoxypyridazin-3-amine (4.50 g, 29.4 mmol), 2-bromo-1-[4-(2-methoxyethoxy)phenyl]ethanone (8.03 g, 29.4 mmol) and ethanol (280 mL) was heated under reflux for 2.5 hours. The mixture was cooled and sodium bicarbonate (2.50 g, 30 mmol) added. The mixture was stirred at room temperature for 15 hours, heated under reflux for 1 hour, then cooled and evaporated. The residue was extracted with chloroform (150 mL) and the extract washed with saturated, aqueous, sodium chloride solution (50 mL), dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel. Elution with 1-2% methanol in dichloromethane afforded a green/brown solid. Treatment with decolourising charcoal in diethyl ether solution (three times) and recrystallization from cyclohexane gave Compound 63 (3.95 g, 41%) as pale green crystals. M.p. 82.5-84° C. 1H n.m.r. (CDCl3) δ 1.06, t, J=7.2 Hz, 3H; 1.75-1.94, m, 2H; 3.47, s, 3H; 3.74-3.81, m, 2H; 4.14-4.21, m, 2H; 4.27, t, J=6.6 Hz, 2H; 6.68, d, J=9.3 Hz, 1H; 7.00, d, J=8.8 Hz, 2H; 7.76-7.88, m, 3H; 7.94, s, 1H. Mass spectrum (APCI+) m/z 328 (M+H, 100%).

Provenance & Evidence