Sodium Hydroxide → 1-(4-fluorophenyl)-1H-pyrazole-3-carboxylic acid

HRID 1755259Notes

Reaction equation

HRID 1755259 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([O:15]CC)=[O:14])=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>CCO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14129372ethyl 1-(4-fluorophenyl)-1H-pyrazole-3-carboxylate

Product 1

HCID 289740501-(4-fluorophenyl)-1H-pyrazole-3-carboxylic acidYield 52%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 1-(4-fluorophenyl)pyrazole-3-carboxylate (0.92 g, 3.9 mmol, 1 eq) in 18 mL of EtOH/H2O (1.5:1) was added NaOH (0.47 g, 11.8 mmol, 3 eq). The reaction mixture was heated at 50° C. for 1 h then quenched with H2O and extracted with ethyl acetate. The combined organic layers were concentrated and purified by silica gel column chromatography (EtoAc:MeOH 3:1) to provide 1-(4-fluorophenyl)pyrazole-3-carboxylic acid (0.42 g, 2.0 mmol, 52%).

Workup

  1. customthen quenched with H2O
  2. extractionextracted with ethyl acetate
  3. concentrationThe combined organic layers were concentrated
  4. custompurified by silica gel column chromatography (EtoAc:MeOH 3:1)

Sources & evidence

ORD record
ord-d1a13889a9fe4ca88c05e7152efac08e
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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