Water → 1-(4-fluorophenyl)-3-methyl-1H-pyrazole-4-carboxylic acid

HRID 1744469Notes

Reaction equation

HRID 1744469 reaction equation
O.[F:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[C:12]([C:14]([O:16]CC)=[O:15])[C:11]([CH3:19])=[N:10]2)=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[F:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[C:11]([CH3:19])=[N:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 22228060Ethyl 1-(4-fluorophenyl)-3-methylpyrazole-4-carboxylate

Product 1

HCID 222280571-(4-fluorophenyl)-3-methyl-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixed solvent of ethanol (40 ml) and water (40 ml) were added ethyl 1-(4-fluorophenyl)-3-methylpyrazole-4-carboxylate (8.5 g) and sodium hydroxide (1.66 g), and the mixture was stirred at a refluxing temperature for 2 h. After the reaction, 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, melting point: 194–195° C.

Workup

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

Sources & evidence

ORD record
ord-acb36e67ecfe48ac937268c9f2f5f074
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

Loading…