Pyrazole-4-carboxylic acid → Methyl 1H-pyrazole-4-carboxylate

HRID 862479Notes

Reaction equation

HRID 862479 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=[O:7])[CH:3]=[N:2]1.[CH3:9][O-].[Na+]>CO.S(=O)(=O)(O)O>[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 3015937Pyrazole-4-carboxylic acidHCID 10942334Sodium Methoxide

Product 1

HCID 9793760Methyl 1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

4-Pyrazolecarboxylic acid (514 mg) was dissolved in methanol (10 ml) and sulfuric acid (0.25 ml), and the mixture was stirred at room temperature for 2 hours, followed by refluxing under heating for 4 hours. After cooling, a 28% solution (0.95 ml) of sodium methylate in methanol was added to the reaction mixture for neutralization and the solvent was distilled away. Chloroform was added to the residue, and the residue was washed with water and brine and dried over anhydrous magnesium sulfate. The solvent was distilled away to give 433 mg of the title compound.

Workup

  1. temperatureby refluxing
  2. temperatureunder heating for 4 hours
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled away
  5. additionChloroform was added to the residue
  6. washthe residue was washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled away

Sources & evidence

ORD record
ord-03a04da955174a06bbf4cc1d968eb199
Source dataset
uspto-grants-1998_02
Patent number
US05719155

Reaction notes

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