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

HRID 1744478Notes

Reaction equation

HRID 1744478 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][C:10]([C:14]([O:16]CC)=[O:15])=[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])=[CH:11][C:10]([C:14]([OH:16])=[O:15])=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22228105HCID 22228105, compound

Product 1

HCID 222279451-(4-fluorophenyl)-5-methyl-1H-pyrazole-3-carboxylic acidYield 78.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 1-(4-fluorophenyl)-5-methylpyrazole-3-carboxylate (3 g) was dissolved in a mixed solvent of ethanol (15 ml) and water (15 ml) and sodium hydroxide (0.6 g) was added. The mixture was stirred at a refluxing temperature for 30 min. Ethanol was evaporated and to the residue was added dilute hydrochloric acid. The obtained solid was recrystallized from aqueous methanol solution to give the title compound (2.1 g), melting point: 177° C.

Workup

  1. additionwas added
  2. customEthanol was evaporated and to the residue
  3. additionwas added dilute hydrochloric acid
  4. customThe obtained solid was recrystallized from aqueous methanol solution

Sources & evidence

ORD record
ord-494ce2169e4e4a6d8f1a52ecca676ac1
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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