Acrylamide → Phenidone

HRID 2393342Notes

Reaction equation

HRID 2393342 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9](N)(=[O:12])[CH:10]=[CH2:11].[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]1([N:7]2[CH2:11][CH2:10][C:9](=[O:12])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6579AcrylamideHCID 7516PhenylhydrazineHCID 14797Potassium Hydroxide

Product 1

HCID 7090Phenidone

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

Phenylhydrazine (10.8 g, 0.1 mol), and acrylamide (7.8 g, 0.11 mol), pulverized potassium hydroxide (12.5 g, 0.22) and a catalytic amount of tetrabutylammonium bromide is refluxed for 30 minutes. The precipitate is filtered and washed with toluene. The crystalline sold is dissolved in water. Acidification with acetic acid, filtration and drying gives 1-phenyl-3-pyrazolidone.

Workup

  1. filtrationThe precipitate is filtered
  2. washwashed with toluene
  3. dissolutionThe crystalline sold is dissolved in water
  4. filtrationAcidification with acetic acid, filtration
  5. customdrying

Sources & evidence

ORD record
ord-a82caac1fad34dcb8cdc22597bbf516d
Source dataset
uspto-grants-1998_09
Patent number
US05807863

Reaction notes

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