Hydrazine hydrate (1:1) → methyl 3-phenyl-1H-pyrazole-5-carboxylate

HRID 2369835Notes

Reaction equation

HRID 2369835 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4](O)=[CH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[NH2:17][NH2:18]>CCO>[C:7]1([C:6]2[CH:5]=[C:4]([C:3]([O:2][CH3:1])=[O:15])[NH:18][N:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178501817HCID 178501817, compound

Product 1

HCID 644585methyl 3-phenyl-1H-pyrazole-5-carboxylateYield 51.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-hydroxy-4-oxo-4-phenyl-but-2-enoic acid methyl ester (12.0 g, 58.2 mmol) in EtOH (30 ml) was added hydrazine monohydrate (2.84 mL, 58.2 mmol) and the mixture was heated at reflux for 5 h. The reaction mixture was cooled to room temperature and filtered in vacuo. The precipitate was washed with EtOH to give the desired product (6.02 g, 51.5% yield): MS (EI) for C11H10N2O2: 203.08 (MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 5 h
  3. filtrationfiltered in vacuo
  4. washThe precipitate was washed with EtOH

Sources & evidence

ORD record
ord-c670649d0c0b46b587adfefb8020a4f2
Source dataset
uspto-grants-2014_04
Patent number
US08710038B2

Reaction notes

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