Hydrochloric Acid → HCID 57893421, compound

Participants

Reaction Steps

Ethyl 2-(2-cyclopropylethyl)-5-hydroxy-3-oxo-6-phenyl-2,3-dihydro-4-pyridazinecarboxylate. Sodium hydride (0.040 g of a 60% oil suspension, 1.00 mmol) was added to a stirred solution of ethyl 5-hydroxy-3-oxo-6-phenyl-2,3-dihydro-4-pyridazinecarboxylate (example 4(b), 0.100 g, 0.384 mmol) in dimethylformamide (1.5 mL) under nitrogen. After 15 min stirring at room temperature, the mixture was cooled in an ice bath and (2-bromoethyl)cyclopropane (0.057 g, 0.384 mmol) added. The mixture was stirred for 18 h while warming to room temperature, then poured into 0.1M aqueous hydrochloric acid (50 mL) and extracted with ethyl acetate. The extracts were washed with water and brine, then dried (MgSO4), evaporated under reduced pressure and the residue chromatographed (silica gel, 1-5% methanol/dichloromethane) to give the title compound (0.067 g, 53%) as a colourless gum. 1H NMR (400 MHz, DMSO-d6) δ ppm −0.05-0.06 (m, 2H) 0.34-0.45 (m, 2H) 0.64-0.78 (m, 1H) 1.29 (t, J=7.07 Hz, 3H) 1.62 (q, J=7.07 Hz, 2H) 4.14 (t, J=7.20 Hz, 2H) 4.31 (q, J=7.07 Hz, 2H) 7.41-7.52 (m, 3H) 7.63-7.71 (m, 2H) 12.42 (br. s., 1H).

Provenance & Evidence