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

HRID 1060178Notes

Reaction equation

HRID 1060178 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-2d3e1ed335694811bf9269de176abcba
Source dataset
uspto-grants-2003_02
Patent number
US06521603B2

Reaction notes

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