Phenylhydrazine → 4-(5-amino-1-phenyl-1H-pyrazole-3-yl)-benzoic acid methyl ester

HRID 1860521Notes

Reaction equation

HRID 1860521 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11][C:12]#[N:13])=[CH:6][CH:5]=1.[C:16]1([NH:22][NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]([NH2:13])[N:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:23]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 736021Methyl 4-(cyanoacetyl)benzoate

Product 1

HCID 698301914-(5-amino-1-phenyl-1H-pyrazole-3-yl)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl-4-(cyanoacetyl)benzoate (5.0 g, 24.6 mmol) and phenylhydrazine (2.42 ml, 24.6 mmol) in ethanol (100 ml) was heated to reflux for 20 hours. The mixture was cooled and the product was collected by filtration. The product was purified by trituration in hot acetonitrile, cooled and collected by filtration to give the product 4-(5-amino-1-phenyl-1H-pyrazole-3-yl)-benzoic acid methyl ester as a colorless solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. temperatureThe mixture was cooled
  4. filtrationthe product was collected by filtration
  5. customThe product was purified by trituration in hot acetonitrile
  6. temperaturecooled
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-891129d41585444f8cf20e5012374e98
Source dataset
uspto-grants-2003_03
Patent number
US06531478B2

Reaction notes

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