[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)[CH:5]=[CH:6][CH:7]=1.[CH3:18][NH:19][NH2:20]>C(O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]2[N:19]([CH3:18])[N:20]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1To a 100 ml round bottom flask equipped with a magnetic stirrer and reflux condensor was charged 1.0 g (0.0045 moles) of 3-hydroxychalcone, and 25 mls of absolute ethanol. To this solution was then added 0.21 g (0.0045 moles) of methyl hydrazine in one portion. The reaction was then heated to reflux for two hours, then cooled. The solvent was removed under reduced pressure to afford 1.1 g of 5-(3-hydroxyphenyl)-1-methyl-3-phenyl-2-pyrazoline as a thick brown oil. 97% yield.
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