Ammonia → HCID 22609937, compound

Participants

Reaction Steps

Concentrated sulphuric acid (10.7 ml, 0.2 mol) was added to a solution of 3,6-dichloropyridazine (10 g, 67 mmol) in water (250 ml). This mixture was heated to 70° C. before addition of 1-methylcyclohexane carboxylic acid (9.67 g, 68 mmol). Silver nitrate (2.3 g, 13.5 mmol) in water (5 ml) was then added over one minute followed by ammonium persulphate (45.6 g, 0.2 mol) in water (95 ml) added over 20 minutes. Upon complete addition, the reaction was stirred for an additional 5 minutes and then allowed to cool to room temperature. The mixture was cooled to 0° C. (ice/water bath) and basified with concentrated aqueous ammonia solution (internal temperature <10° C.). The aqueous phase was extracted with dichloromethane (3×350 ml) and the combined extracts washed with brine (350 ml), dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica using 0→5% ethyl acetate in dichloromethane as eluent to give the required product (5.93 g): 1H NMR (250 MHz, CDCl3) δ 1.33-1.74 (6H, m), 1.43 (3H, s), 1.80-1.96 (2H, m), 1.97-2.12 (2H, m), 7.49 (1H, s); MS (ES+) m/e 249 [MH]+, 247 [MH]+, 245 [MH]+.

Provenance & Evidence