Hydrazine hydrate (1:1) → 4,5-dihydro-6-[4-(2-acetoxypropyl)phenyl]-3(2H)-pyridazinone

Reaction equation

[C:1]([O:4][CH:5]([CH3:20])[CH2:6][C:7]1[CH:19]=[CH:18][C:10]([C:11]([CH2:13][CH2:14][C:15](O)=[O:16])=O)=[CH:9][CH:8]=1)(=[O:3])[CH3:2].O.[NH2:22][NH2:23]>C(O)(=O)C.O>[C:1]([O:4][CH:5]([CH3:20])[CH2:6][C:7]1[CH:19]=[CH:18][C:10]([C:11]2[CH2:13][CH2:14][C:15](=[O:16])[NH:22][N:23]=2)=[CH:9][CH:8]=1)(=[O:3])[CH3:2]

Participants

Procedure

A solution of 3-[4-(2-acetoxypropyl)benzoyl]propionic acid (0.8 g) in glacial acetic acid (10 ml) was treated with hydrazine hydrate (1 ml). The resulting solution was stirred and heated under reflux for 1 hr., cooled, diluted with water, and extracted into ethyl acetate. The organic layer was washed with NaHCO3 solution, dried (MgSO4) and evaporated to give 4,5-dihydro-6-[4-(2-acetoxypropyl)phenyl]-3(2H)-pyridazinone as a colourless oil.