Water → HCID 178524957, compound

HRID 1058013Notes

Reaction equation

HRID 1058013 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>[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 178524957HCID 178524957, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 4-[3-(4-fluorophenyl)-5-methyl-1H-pyrazol-4-yl]pyridine prepared as set forth in Example A-4 (5.83 g, 24.0909 mmol) and potassium permanganate (7.6916 g, 48.1818 mmol) in water (7.5 ml) and tert-butanol (10 ml) was heated at reflux for 6 hours (or until all the potassium permanganate was consumed). The mixture was then stirred at room temperature overnight and then diluted with water (150 ml). Manganese dioxide was removed from the mixture by filtration. The filtrate was extracted with ethyl acetate to remove unreacted starting material. The aqueous layer was acidified with 1N HCl to increase the pH to about 6. A white precipitate formed, was collected by filtration, washed with water, and dried in a vacuum oven to give 5-(4-fluorophenyl)-4-(4-pyridinyl)-1H-pyrazole-3-carboxylic acid (isolated as the monohydrate salt) (2.9777 g, 43.7%). Anal. Calc'd for C15H10N3FO2.H2O (283+18): 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)
  4. additiondiluted with water (150 ml)
  5. customManganese dioxide was removed from the mixture by filtration
  6. extractionThe filtrate was extracted with ethyl acetate
  7. customto remove unreacted
  8. temperatureto increase the pH to about 6
  9. customA white precipitate formed
  10. filtrationwas collected by filtration
  11. washwashed with water
  12. customdried in a vacuum oven

Sources & evidence

ORD record
ord-b1d5ee4752924bf2bed119f363359d16
Source dataset
uspto-grants-2003_02
Patent number
US06514977B1

Reaction notes

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