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

HRID 378111Notes

Reaction equation

HRID 378111 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-c42ea6e28eda42e499f9f02403e55d63
Source dataset
uspto-grants-2000_02
Patent number
US06028101

Reaction notes

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