Phenylhydrazine → 5-Methyl-2-phenyl-3-pyrzolidinone

HRID 1954208Notes

Reaction equation

HRID 1954208 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]1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 637090Crotonic Acid

Product 1

HCID 4590355-Methyl-2-phenyl-3-pyrzolidinoneYield 63%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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%).

Workup

  1. washThe solution was washed twice with 100 ml of 10% aqueous solution of sodium hydroxide and once with 100 ml of water
  2. customfollowed by evaporation of the ether
  3. customThe resulting solid was dried under reduced pressure
  4. customrecrystallized from toluene

Sources & evidence

ORD record
ord-7a7bd770b2c94f6f8837212e7ee42c9c
Source dataset
uspto-grants-2000_09
Patent number
US06121305

Reaction notes

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