Sodium Hydroxide → 5-methyl-1H-pyrazole-4-carboxylic acid

HRID 2067951Notes

Reaction equation

HRID 2067951 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+]>CCO>[CH3:11][C:10]1[NH:9][N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 227598ethyl 3-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 5576005-methyl-1H-pyrazole-4-carboxylic acidYield 74.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A portion of the 5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (2.7 g, 18 mmol) is dissolved in EtOH (15 mL) and treated with aqueous sodium hydroxide solution (2.0 N solution, 20 mL, 40 mmol). The reaction is heated at 80° C. for 4 hours. The resultant mixture is then cooled and concentrated in vacuo to remove most of the EtOH. The crude is then acidified with 6N HCl until a precipitate is formed and filtered to afford 5-methyl-1H-pyrazole-4-carboxylic acid as a colorless solid (1.7 g, 74%).

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove most of the EtOH
  3. customis formed
  4. filtrationfiltered

Sources & evidence

ORD record
ord-0c0b6ee929594f30b037894e27214650
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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