Sodium Hydroxide → 1-Phenyl-1H-pyrazole-5-carboxylic acid

HRID 1090809Notes

Reaction equation

HRID 1090809 reaction equation
[C:1]1([N:7]2[C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([N:7]2[C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 6424675Ethyl 1-phenyl-1H-pyrazole-5-carboxylate

Product 1

HCID 2370561-Phenyl-1H-pyrazole-5-carboxylic acidYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.4 g of ethyl 1-phenylpyrazole-5-carboxylate from Example 1 were stirred for 6 hours at room temperature with 10 ml of 16.5% strength aqueous NaOH and 10 ml of ethanol; the ethanol was removed by distillation, the aqueous phase was extracted twice with 10 ml of toluene, and the pH was adjusted to 3 using concentrated HCl. The precipitate was filtered off under suction, washed with a little water and dried: 3.1 g of product of boiling point 182°-183° C. were obtained.

Workup

  1. customthe ethanol was removed by distillation
  2. extractionthe aqueous phase was extracted twice with 10 ml of toluene
  3. filtrationThe precipitate was filtered off under suction
  4. washwashed with a little water
  5. customdried

Sources & evidence

ORD record
ord-f3576e277ae6453ba71ef2be29dddc90
Source dataset
uspto-grants-1992_01
Patent number
US05082949

Reaction notes

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