Sodium Hydroxide → 3-acetyl-1H-pyrazole-5-carboxylic acid

HRID 925408Notes

Reaction equation

HRID 925408 reaction equation
[C:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([O:11]CC)=[O:10])[CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([OH:11])=[O:10])[CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178468948HCID 178468948, compound

Product 1

HCID 167673463-acetyl-1H-pyrazole-5-carboxylic acidYield 87.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 5-acetyl-1H-pyrazole-3-carboxylate (0.050 g, 0.274 mmol) was dissolved in EtOH (5 mL) and treated with a 2 M solution of NaOH (0.5 mL, 1 eq.) at reflux temperature for 3 h. Solvent was evaporated to dryness and the residue dissolved in H2O. After treatment with 2M HCl the resulting precipitate was extracted with DCM. The organic phase was dried on Na2SO4 and concentrated to dryness to give the title compound (37 mg, 87% yield) as a white solid.

Workup

  1. temperatureat reflux temperature for 3 h
  2. customSolvent was evaporated to dryness
  3. dissolutionthe residue dissolved in H2O
  4. extractionAfter treatment with 2M HCl the resulting precipitate was extracted with DCM
  5. customThe organic phase was dried on Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2e684046b5b54189a1213aef3f47c92d
Source dataset
uspto-grants-2016_03
Patent number
US09284298B2

Reaction notes

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