Sodium Hydroxide → N-Methyl-3,5-difluoromethyl-4 pyrazolecarboxylic acid

HRID 2283196Notes

Reaction equation

HRID 2283196 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH2:14][F:15])=[N:8][N:9]([CH3:13])[C:10]=1[CH2:11][F:12])=[O:5])C.[OH-].[Na+]>C(O)C>[CH3:13][N:9]1[C:10]([CH2:11][F:12])=[C:6]([C:4]([OH:5])=[O:3])[C:7]([CH2:14][F:15])=[N:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90002518N-Methyl-3,5-difluoromethyl-4-pyrazolecarboxylic acid ethyl ester

Product 1

HCID 89727263N-Methyl-3,5-difluoromethyl-4 pyrazolecarboxylic acidYield 97.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Methyl-3,5-difluoromethyl-4-pyrazolecarboxylic acid ethyl ester (0.5 g, 2.0 mmol) in ethanol (3 ml) was admixed gradually with an 8N aqueous sodium hydroxide solution (0.8 ml) and stirred at room temperature for 2 h. The solvent was removed by rotary evaporation; the residue was taken up in water (10 ml) and extracted with diethyl ether (10 ml). Acidification to pH 1 with 6M HCl was followed by extraction with ethyl acetate (3×10 ml). The combined organic phases were dried over sodium sulphate and filtered, and the solvent was removed by rotary evaporation. N-Methyl-3,5-difluoromethyl-4 pyrazolecarboxylic acid (0.44 g, 1.95 mmol, 97%) was isolated as a colourless solid.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. extractionextracted with diethyl ether (10 ml)
  3. extractionAcidification to pH 1 with 6M HCl was followed by extraction with ethyl acetate (3×10 ml)
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-97aeae675fa448dbb237fbf1ecea05ba
Source dataset
uspto-grants-2015_09
Patent number
US09145370B2

Reaction notes

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