Phenylhydrazine → 5-Methyl-2-phenyl-3-pyrzolidinone
Reaction equation
[C:1]([OH:6])(=O)/[CH:2]=[CH:3]/[CH3:4].[C:7]1([NH:13][NH2:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCOCC>[CH3:4][CH:3]1[CH2:2][C:1](=[O:6])[N:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:14]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 155 °C
Procedure
17.2 g of crotonic acid (MW 86.09, 0.2 mol) was added to 21.6 g of phenylhydrazine (MW 108.14, 0.2 mol), and the mixture was stirred for one hour while heating at 150-160° C. The reaction solution was dissolved in 500 ml of ether. The solution was washed twice with 100 ml of 10% aqueous solution of sodium hydroxide and once with 100 ml of water, followed by evaporation of the ether. The resulting solid was dried under reduced pressure and recrystallized from toluene to obtain 20.31 g of 3-methyl-1-phenyl-5-pyrazolidone (MW 176.0, 0.126 mol, 58%).