Piperidinium acetate → HCID 57893425, compound

Participants

Reaction Steps

Ethyl 5-hydroxy-3-oxo-6-phenyl-2,3-dihydro-4-pyridazinecarboxylate. A 1 M solution of piperidinium acetate in 5% ethanol/toluene (1.10 mL, 1.10 mmol) was added to a solution of the compound from example 4(a) (0.350 g, 1.14 mmol) in toluene (10 mL) and the mixture stirred under reflux for 1 h. Diazabicyclo[5.4.0]undec-7-ene (0.30 mL, 2.00 mmol) was added and the reflux continued for 2 h. After cooling, the mixture was partitioned between 1M aqueous hydrochloric acid and ethyl acetate. The extracts were dried (MgSO4), evaporated under reduced pressure and the residue chromatographed (silica gel, 2-8% methanol/dichloromethane). The partially purified product was triturated with ether to give the title compound (0.115 g, 39%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.30 (t, J=7.20 Hz, 3H) 4.32 (q, J=7.16 Hz, 2H) 7.43-7.49 (m, 3H) 7.64-7.67 (m, 2H) 13.05 (s, 1H).

Provenance & Evidence