Phenylhydrazine → Ethyl 3-amino-1-phenyl-1H-pyrazole-4-carboxylate

HRID 914449Notes

Reaction equation

HRID 914449 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5](=[CH:8]OCC)[C:6]#[N:7])[CH3:2].[C:13]1([NH:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[C:6]([NH2:7])=[N:20][N:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=1)=[O:12])[CH3:2]

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester

Product 1

HCID 14590586Ethyl 3-amino-1-phenyl-1H-pyrazole-4-carboxylateYield 80.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(Ethoxymethylene)-2-cyanoacetic acid ethyl ester (78.2 g) and phenylhydrazine (50.0 g) were dissolved in ethanol (500 mL), and the mixture was refluxed for 3 hr. After cooling, the reaction mixture was concentrated under reduced pressure. Hexane (500 mL) was added, to the residue, and the residue was washed by suspending and filtered. The obtained solid was vacuum dried to give the title compound (86.0 g) as a white solid.

Workup

  1. temperaturethe mixture was refluxed for 3 hr
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionHexane (500 mL) was added, to the residue
  5. washthe residue was washed
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-3fd1a67ddbab41b68258aec6c83f906e
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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