Water → 1-(4-fluorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid

HRID 1744466Notes

Reaction equation

HRID 1744466 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([O:16]CC)=[O:15])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].O>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=[O:15])[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 3654436HCID 3654436, compound

Product 1

HCID 42702631-(4-fluorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acidYield 78.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Then, ethyl 1-(4-fluorophenyl)-5-methylpyrazole-4-carboxylate (17.7 g) and sodium hydroxide (3.5 g) were added to a mixed solvent of ethanol (80 ml)-water (80 ml), and the mixture was stirred at a refluxing temperature for 2 h. After the reaction, ethanol was evaporated and dilute hydrochloric acid was added. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was recrystallized from ethyl acetate to give the title compound (12.3 g), melting point: 165–166° C.

Workup

  1. customwas evaporated
  2. additiondilute hydrochloric acid was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ee36f1bc9aae4009b79ac498e69dfc19
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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