Sodium Hydroxide → 1-Phenyl-1H-pyrazole-3-carboxylic acid

HRID 1178119Notes

Reaction equation

HRID 1178119 reaction equation
[O-:1][Mn](=O)(=O)=O.[K+].[CH3:7][C:8]1[CH:12]=[CH:11][N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]=1.[OH-:19].[Na+]>O>[C:13]1([N:10]2[CH:11]=[CH:12][C:8]([C:7]([OH:1])=[O:19])=[N:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 707833-Methyl-1-phenyl-1H-pyrazoleHCID 516875Potassium Permanganate

Product 1

HCID 123708741-Phenyl-1H-pyrazole-3-carboxylic acidYield 44.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

KMnO4 (1.2 g, 7.6 mmol) was added portionwise to a stirred solution of 3-Methyl-1-phenyl-1H-pyrazole (100 mg, 0.63 mmol) and NaOH (504 mg, 12.6 mmol) in H2O (4 mL). The resulting mixture was heated to 85° C. for 48 hrs. The reaction mixture was filtered, filtrate was acidified with 30% aqueous HCl solution, extracted the aqueous layer with EtOAc. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was purified by washing with hexane to afford 53 mg (44.53% yield) of 1-phenyl-1H-pyrazole-3-carboxylic acid. 1H NMR (DMSO-d6): δ 8.6 (d, 1H), 7.9 (d, 2H), 7.6-7.5 (t, 2H), 7.4 (t, 1H), 6.96 (d, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. extractionextracted the aqueous layer with EtOAc
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get the residue
  6. customThe obtained residue was purified
  7. washby washing with hexane

Sources & evidence

ORD record
ord-ba1ce0e2994b4c648b7210d449061c20
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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