C1([C:4]([C:13]([C:15]([CH:24]2[CH2:26]C2)=CC2C=CC=C(O)C=2)=O)=[CH:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=2)CC1.O.[NH2:28][NH2:29]>O>[CH:15]1([C:13]2[CH2:4][CH:5]([C:6]3[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=3)[NH:29][N:28]=2)[CH2:24][CH2:26]1To a 500 ml round bottom flask equipped with magnetic stirrer and reflux condenser was charged 13.2 g (0.0702 moles) of cyclopropyl 3-hydroxystyrylketone 150 mls of water and 3.5 g (0.0702 moles) of hydrazine monohydrate. The reaction was refluxed for a total of 2 hours, after which it was cooled and diluted with an additional 200 mls of water. The resulting solid was collected by vacuum filtration, washed with water and hexane, and dried in vacuuo at 40° C. overnight to afford 9.6 g of 3-cyclopropyl-5-(3-hydroxyphenyl)-2-pyrazoline as a tan solid at a 68% isolated yield.
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