Benzyl Alcohol → HCID 21706541, compound

Participants

Reaction Steps

To a stirred solution of 4-carboxy-2-(4-methoxybenzyl)-5-methyl-3-pyridazinone (0.50 g, 1.8 mmol) in benzene (20 mL) was added diphenylphosphoryl azide (0.63 g, 2.3 mmol) and triethylamine (0.76 mL, 5.5 mmol). The mixture was stirred at rt for 30 minutes, heated under reflux for 30 minutes, and cooled. Benzyl alcohol (0.24 g, 2.2 mmol) was added, and the mixture was heated under reflux for 17 hours. The mixture was cooled, washed with aqueous citric acid, water, aqueous sodium bicarbonate and brine, dried, filtered and evaporated. Chromatography of the residue over silica gel (15% to 25% ethyl acetate/hexane) gave 4-benzyloxycarbonylamino-2-(4-methoxybenzyl)-5-methyl-3-pyridazinone (0.39 g, 1.0 mmol, 56%).

Provenance & Evidence