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

HRID 1816613Notes

Reaction equation

HRID 1816613 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([O:9]CC)=[O:8])=[CH:5][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:3]1.[OH-].[Na+].Cl>C(O)C>[CH3:1][N:2]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4166529Ethyl 1-methyl-3-phenyl-1H-pyrazole-5-carboxylate

Product 1

HCID 75376251-methyl-3-phenyl-1H-pyrazole-5-carboxylic acidYield 104.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.12 g of ethyl 1-methyl-3-phenyl-1H-5-pyrazolecarboxylate was dissolved in 5 ml ethanol. 1 ml of 5N aqueous sodium hydroxide solution was added thereto, followed by heating under reflux for 1 hour. The reaction solution 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 0.11 g of 1-methyl-3-phenyl-1H-5-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-fa0326720bd64c229e26436350aa4445
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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