Sodium Hydroxide → 1-(4-fluorophenyl)-1H-pyrazole-4-carboxylic acid

HRID 1744471Notes

Reaction equation

HRID 1744471 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14994516Ethyl 1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 31596171-(4-fluorophenyl)-1H-pyrazole-4-carboxylic acidYield 95.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 1-(4-fluorophenyl)pyrazole-4-carboxylate (10.6 g) was dissolved in a mixed solvent of ethanol (80 ml) and water (80 ml), and sodium hydroxide (2.2 g) was added. The mixture was stirred at a refluxing temperature for 30 min. After evaporation of ethanol, dilute hydrochloric acid was added to the residue. The obtained solid was recrystallized from aqueous methanol solution to give the title compound (8.9 g), melting point: 244–247° C.

Workup

  1. additionwas added
  2. customAfter evaporation of ethanol, dilute hydrochloric acid
  3. additionwas added to the residue
  4. customThe obtained solid was recrystallized from aqueous methanol solution

Sources & evidence

ORD record
ord-784da902b3d9492aa6c5c20db22b11e8
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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