Sodium Hydroxide → 1-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylic acid

HRID 1744475Notes

Reaction equation

HRID 1744475 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([O:16]CC)=[O:15])[C:10]([CH3:19])=[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[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=[O:15])[C:10]([CH3:19])=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 1491284ethyl 1-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylate

Product 1

HCID 14913551-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylic acidYield 83.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Then, ethyl 1-(4-fluorophenyl)-3,5-dimethylpyrazole-4-carboxylate (15.5 g) was dissolved in a mixed solvent of ethanol (30 ml) and water (30 ml). Sodium hydroxide (2.75 g) was added and 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 (11.5 g), melting point: 219–220° C.

Workup

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

Sources & evidence

ORD record
ord-b5a3d5d135e14f228af778b1af7f9c0d
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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