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

HRID 1816621Notes

Reaction equation

HRID 1816621 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([O:9]CC)=[O:8])[N: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][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=[O:8])[N: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 2746772Ethyl 3-methyl-1-phenylpyrazole-5-carboxylate

Product 1

HCID 27695923-methyl-1-phenyl-1H-pyrazole-5-carboxylic acidYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.37 g of ethyl 3-methyl-1-phenyl-1H-5-pyrazolecarboxylate was dissolved in 10 ml ethanol, and 1 ml of 5N sodium hydroxide was added, followed by heating under reflux for 1 hour. The reaction solution was ice-cooled and neutralized with 2N hydrochloric acid, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated, to give 0.26 g of 3-methyl-1-phenyl-1H-5-pyrazolecarboxylic acid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1 hour
  3. temperaturecooled
  4. extractionby extracting 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-f9492ed19d544377aa5c5ada0dda50b3
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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