Sulfuric Acid → 2-(4-Chlorophenyl)pyrazolidin-3-one

HRID 1388334Notes

Reaction equation

HRID 1388334 reaction equation
[C:1](=[O:4])(O)[O-].[Na+].Cl.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][NH2:15])=[CH:10][CH:9]=1.[C:16](#N)[CH:17]=C.S(=O)(=O)(O)O.[OH-].[Na+]>O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:1](=[O:4])[CH2:17][CH2:16][NH:15]2)=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 7855AcrylonitrileHCID 14798Sodium HydroxideHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 132721582-(4-Chlorophenyl)pyrazolidin-3-oneYield 28.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4.2 grams (0.05 mole) of sodium bicarbonate in 25 ml of water, 8.9 grams (0.05 mole) of (4-chlorophenyl)hydrazine hydrochloride was added portionwise. After complete addition the mixture was stirred until gas evolution ceased. To this mixture was added 5.5 grams (0.1 mole) of acrylonitrile and the total heated at 80° C. for 4.5 hours. The mixture was cooled and added to a solution of 9.8 grams of concentrated sulfuric acid in 29 ml of water at room temperature. The resultant mixture was heated for one hour at 40° C. and then at reflux for 2.5 hours. This mixture was cooled and added dropwise to a solution of 7.8 grams of sodium hydroxide in 11 ml of water, cooled by an ice bath and stirred for one hour after complete addition. A precipitate formed which was collected by filtration. The filter cake was washed with water, dried under reduced pressure and purified by recrystallization from ethanol to yield 2.78 grams of 2-(4-chlorophenyl)-3-pyrazolidinone (mp 120°-122° C.).

Workup

  1. additionAfter complete addition the mixture
  2. temperatureThe mixture was cooled
  3. temperatureat reflux for 2.5 hours
  4. temperatureThis mixture was cooled
  5. temperaturecooled by an ice bath
  6. stirringstirred for one hour
  7. additionafter complete addition
  8. customA precipitate formed which
  9. filtrationwas collected by filtration
  10. washThe filter cake was washed with water
  11. customdried under reduced pressure
  12. custompurified by recrystallization from ethanol

Sources & evidence

ORD record
ord-b482905d15ac401da396e1f57903e642
Source dataset
uspto-grants-1984_02
Patent number
US04431659

Reaction notes

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