Sodium Hydroxide → 5-ethyl-1-phenyl-1H-pyrazole-4-carboxylic acid

HRID 1253478Notes

Reaction equation

HRID 1253478 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[CH:5][C:4]=1[C:14]([O:16]C)=[O:15])[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[CH:5][C:4]=1[C:14]([OH:16])=[O:15])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67207603HCID 67207603, compound

Product 1

HCID 80788835-ethyl-1-phenyl-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 5-ethyl-1-phenyl-1H-pyrazole-4-carboxylate (315 mg, 1.37 mmol) in ethanol (5 ml) was added 10M sodium hydroxide (0.410 ml, 4.10 mmol). The reaction mixture was heated to 80° C. After 3 hours, the reaction mixture was cooled and quenched with 1N HCl until the pH ˜1. The reaction mixture was diluted with chloroform and water, the organics were separated, then dried over magnesium sulfate, filtered, and concentrated to afford 5-ethyl-1-phenyl-1H-pyrazole-4-carboxylic acid.

Workup

  1. temperaturethe reaction mixture was cooled
  2. customquenched with 1N HCl until the pH ˜1
  3. additionThe reaction mixture was diluted with chloroform and water
  4. customthe organics were separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6904232f0f274a919de6817a0c1e4aa0
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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