Ethanol → 1-(4-chlorophenyl)pyrazolidin-3-one

HRID 582271Notes

Reaction equation

HRID 582271 reaction equation
[C:1]([O:5]CC)(=O)[CH:2]=[CH2:3].[O-]CC.[Na+].C(O)C.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][NH2:23])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:3][CH2:2][C:1](=[O:5])[NH:23]2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8821Ethyl AcrylateHCID 70624(4-Chlorophenyl)hydrazineHCID 2723922Sodium ethoxide

Product 1

HCID 28015501-(4-chlorophenyl)pyrazolidin-3-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

90 g (0.9 mol) of ethyl acrylate are added dropwise at 40°-45° C. to a mixture of 15.9 g (234 mmol) of sodium ethoxide, 110 ml of ethanol, 110 ml of toluene and 25.7 g (180 mmol) of 4-chlorophenylhydrazine and the mixture is subsequently stirred for 1 hour at 40° C. The reaction mixture is evaporated to 100 ml and the residue is taken up in water. The resulting mixture is washed a number of times with toluene and the combined organic phases are extracted with 5% strength NaOH. The combined aqueous phases are adjusted to a pH of 6.5 and cooled to 10° C. The solid formed is filtered off with suction, washed with water and dried under reduced pressure.

Workup

  1. customThe reaction mixture is evaporated to 100 ml
  2. washThe resulting mixture is washed a number of times with toluene
  3. extractionthe combined organic phases are extracted with 5% strength NaOH
  4. temperaturecooled to 10° C
  5. customThe solid formed
  6. filtrationis filtered off with suction
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-e0179c3bbabd45d6b05657b203b5e414
Source dataset
uspto-grants-1999_07
Patent number
US05922886

Reaction notes

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