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

HRID 355306

Reaction equation

HRID 355306 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-one

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

One hundred and seventy-six (176) grams of ethyl cinnamate, 108 g of phenylhydrazine, 200 ml of a 28% methanol solution containing sodium methoxide, and 400 ml of acetonitrile were mixed and refluxed with heating in the nitrogen atmosphere for 1 hour. The reaction solution was poured into 2 liters of water and 100 ml of concentrated hydrochloric acid was added, thereby precipitation was formed. This was filtered off and recrystallized with acetonitrile to obtain 180 g of 1-phenyl-5-phenylpyrazolidin-3-one (A) as white crystals. ##STR10## Synthesis of Compound (B)

Workup

  1. additionwere mixed
  2. temperaturerefluxed
  3. temperaturewith heating in the nitrogen atmosphere for 1 hour
  4. additionwas added
  5. customprecipitation
  6. customwas formed
  7. filtrationThis was filtered off
  8. customrecrystallized with acetonitrile

Sources & evidence

ORD record
ord-6d1fd1ca067943bf99054fafecf12191
Source dataset
uspto-grants-1998_11
Patent number
US05830627

Linked notes

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