Ethyl bromoacetate → Pyridazineacetic acid, 1-, (6H), 3-chloro-6-oxo-, ethyl ester

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Reaction Steps

To a solution of 6-chloropyridazin-3-ol (0.5 g, 3.83 mmol, WO2011015629) in DMF (5 mL) was added potassium carbonate (1.059 g, 7.66 mmol, Rankem) followed by ethyl 2-bromoacetate (0.960 g, 5.75 mmol, Spectrochem). The reaction mixture was stirred at RT for 5 h. The reaction mixture was quenched with water (2 mL) and the product was extracted with EtOAc (3×20 mL). Combined organic layers were washed successively with water (20 mL) and brine (20 mL). The organic layer was dried over sodium sulphate and evaporated under vacuum to afford ethyl 2-(3-chloro-6-oxopyridazin-1(6H)-yl)acetate 0.5 g (60.3%) as pale yellow solids. 1H NMR (400 MHz, CDCl3): δ 7.266-7.236 (d, J=12 Hz, 1H), 6.965-6.945 (d, J=7.6 Hz, 1H) 4.819 (s, 2H) 4.273-4.230 (m, 2H) 1.309-1.279 (m, 3H); MS m/z=217.2 (M+H)+.

Provenance & Evidence