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

HRID 1588781Notes

Reaction equation

HRID 1588781 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][N:5]([CH3:13])[N:4]=1.[OH-].[Na+]>CO>[F:15][C:2]([F:1])([F:14])[C:3]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]([CH3:13])[N:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 27829701H-Pyrazole-4-carboxylic acid, 1-methyl-3-(trifluoromethyl)-, ethyl ester

Product 1

HCID 27756651-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acidYield 93.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 3-(trifluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate (22.3 g) was added to a solution of sodium hydroxide (4.4 g) in methanol (200 mL). The contents were heated at reflux for 1 h, then cooled and stirred overnight. The contents were concentrated in vacuo and diluted with water. The aqueous solution was made acidic with 2N HCl and the precipitated white solid was filtered to give the desired acid (18.2 g).

Workup

  1. temperatureThe contents were heated
  2. temperatureat reflux for 1 h
  3. temperaturecooled
  4. concentrationThe contents were concentrated in vacuo
  5. additiondiluted with water
  6. filtrationthe precipitated white solid was filtered

Sources & evidence

ORD record
ord-d65b4e9854d042e298b974c6340e0720
Source dataset
uspto-grants-1993_06
Patent number
US05223526

Reaction notes

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