Water → HCID 178526953, compound

HRID 861065Notes

Reaction equation

HRID 861065 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:11]([CH3:19])[NH:10][N:9]=2)=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=[O:21].[K+].[OH2:26]>C(O)(C)(C)C>[OH2:21].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][N:10]=[C:11]([C:19]([OH:21])=[O:26])[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium Permanganate2×HCID 220373104-[3-(4-fluorophenyl)-5-methyl-1H-pyrazol-4-yl)pyridine

Product 1

HCID 178526953HCID 178526953, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 4-[3-(4-fluorophenyl)-5-methyl-1H-pyrazol-4-yl)pyridine (5.8 g, 24.0909 mmol; prepared as set forth in Example A-4) and potassium permanganate (7.6916 g, 48.1818 mmol) in water (7.5 mL) and tert-butanol (10 mL) was heated to reflux at 95 to 100° C. for 6 hours (or until all the potassium permanganate was consumed) and stirred at room temperature overnight. The mixture was diluted with water (150 mL) and filtered to remove manganese dioxide. The aqueous filtrate (pH>10) was extracted with ethyl acetate to remove unreacted starting material. The aqueous layer was acidified with 1N HCl to a pH of about 6.5. A white precipitate was formed. This precipitate was collected by filtration, dried in air, and then dried in a vacuum oven overnight at 50° C. to give 5-(4-fluorophenyl)-4-(4-pyridinyl)-1H-pyrazole-3-carboxylic acid, monohydrate (2.7677 g, 40.6%). The remaining product (0.21 g, 3.1%) was isolated from the mother liquid by reverse phase chromotograhpy. The total isolated yield of 5-(4-fluorophenyl)-4-(4-pyridinyl)-1H-pyrazole-3-carboxylic acid, monohydrate was 43.7%. Anal. Calc'd for C15H10N3FO2.H2O: C, 59.80; H, 4.01; N, 13.95; Found: C, 59.48; H, 3.26; N, 13.65. MS (MH+): 284 (base peak).

Workup

  1. customprepared
  2. temperaturewas heated
  3. customwas consumed) and
  4. additionThe mixture was diluted with water (150 mL)
  5. filtrationfiltered
  6. customto remove manganese dioxide
  7. extractionThe aqueous filtrate (pH>10) was extracted with ethyl acetate
  8. customto remove unreacted
  9. customA white precipitate was formed
  10. filtrationThis precipitate was collected by filtration
  11. customdried in air
  12. customdried in a vacuum oven overnight at 50° C.

Sources & evidence

ORD record
ord-52323b7c889e491b81ba0d79df75d095
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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