Sodium Hydroxide → 1-Methyl-1H-pyrazole-4-carboxylic acid

HRID 611003Notes

Reaction equation

HRID 611003 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([O:9]CC)=[O:8])[CH:4]=[N:3]1.[OH-].[Na+]>C(O)C>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=[O:8])[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11116265ethyl 1-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 6431601-Methyl-1H-pyrazole-4-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 1-methyl-1H-pyrazole-4-carboxylate (20.2 g, 131 mmol) and NaOH (6.3 g, 158 mmol) in 200 mL absolute ethanol was refluxed for 2 h and stirring was continued at RT for 18 h. After that, the solvent was removed in vacuo. The residue was dissolved in water. The aq solution was washed with ether and acidified with concentrated HCl. The solid was filtered, washed with water and air-dried to give 14.2 g of 1-methyl-1H-pyrazole-4-carboxylic acid in 86% yield.

Workup

  1. customAfter that, the solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in water
  3. washThe aq solution was washed with ether
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customair-dried

Sources & evidence

ORD record
ord-d4c1df2dfb8d46d4ab1a7dc652565226
Source dataset
uspto-grants-1999_12
Patent number
US05998466

Reaction notes

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