Hydrochloric Acid → 1,5-Diphenylpyrazolidin-3-one

HRID 400092

Reaction equation

HRID 400092 reaction equation
[C:1]([O:11]CC)(=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:14]1([NH:20][NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C[O-].[Na+].Cl>O.C(#N)C.CO>[C:14]1([N:20]2[CH:3]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:2][C:1](=[O:11])[NH:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 7649Ethyl 3-phenylprop-2-enoateHCID 10942334Sodium Methoxide

Product 1

HCID 36953731,5-Diphenylpyrazolidin-3-oneYield 75.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

176 g of ethyl cinnamate, 108 g of phenylhydrazine, 200 ml of a 28% methanol solution of sodium methoxide and 400 ml of acetonitrile were mixed and heated under reflux for 1 hour in a nitrogen stream. The reaction solution was poured into 2 l of water and 100 ml of hydrochloric acid was added thereto to produce precipitate. The precipitate was collected by filtration and recrystallized from acetonitrile to obtain 180 g of 1-phenyl-5-phenylpyrazolidin-3-one (A) as white crystals. ##STR14## Synthesis of Compound (B):

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour in a nitrogen stream
  3. additionwas added
  4. customto produce precipitate
  5. filtrationThe precipitate was collected by filtration
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-ff85c450d19e413983e29b84176c2cc6
Source dataset
uspto-grants-1998_10
Patent number
US05827637

Linked notes

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