(4-Fluorophenyl)hydrazine → ethyl 1-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylate

HRID 1744474Notes

Reaction equation

HRID 1744474 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[CH3:10][CH2:11][O:12][C:13]([CH:15]([C:19]([CH3:21])=O)[C:16]([CH3:18])=O)=[O:14]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:19]([CH3:21])=[C:15]([C:13]([O:12][CH2:11][CH3:10])=[O:14])[C:16]([CH3:18])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69982(4-Fluorophenyl)hydrazineHCID 79063Ethyl 2-acetylacetoacetate

Product 1

HCID 1491284ethyl 1-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylateYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Fluorophenylhydrazine (7.75 g) and ethyl diacetoacetate (10.6 g) were added to ethanol (30 ml) and the mixture was refluxed for 3 h. The solvent was evaporated under reduced pressure and diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from a mixed solvent of ethyl acetate-diisopropyl ether to give ethyl 1-(4-fluorophenyl)-3,5-dimethylpyrazole-4-carboxylate (15.5 g), melting point: 59–60° C.

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. customThe solvent was evaporated under reduced pressure and diisopropyl ether
  3. additionwas added to the residue
  4. customcrystallization
  5. customThe crystals were recrystallized from a mixed solvent of ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-eb07b8456e7a456984b4d22e21ffca8d
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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