Hydrochloric Acid → 1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid

HRID 1816614Notes

Reaction equation

HRID 1816614 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][C:4]([C:13]([O:15]CC)=[O:14])=[N:3]1.[OH-].[Na+].Cl>C(O)C>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][C:4]([C:13]([OH:15])=[O:14])=[N:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 7537623Ethyl 1-methyl-5-phenyl-1H-pyrazole-3-carboxylate

Product 1

HCID 75376191-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acidYield 103.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.55 g of ethyl 1-methyl-5-phenyl-1H-3-pyrazolecarboxylate was dissolved in 10 ml ethanol. 2 ml of 5N aqueous sodium hydroxide solution was added thereto, followed by heating under reflux for 1 hour. The reaction mixture was ice-cooled, neutralized with 2N hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated, to give 0.5 g of 1-methyl-5-phenyl-1H-3-pyrazolecarboxylic acid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1 hour
  3. temperaturecooled
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-4db9ea438fbc436c96783e89354272c4
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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