Water → 6-[2-(Trifluoromethyl)phenyl]pyridine-3-carboxylic acid

HRID 363194Notes

Reaction equation

HRID 363194 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][N:10]=1.[Mn]([O-])(=O)(=O)=[O:19].[K+].[OH2:24]>>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:19])=[O:24])=[CH:11][N:10]=1

Participants

4

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 53975108HCID 53975108, compound

Product 1

HCID 247299916-[2-(Trifluoromethyl)phenyl]pyridine-3-carboxylic acid

Procedure

A suspension of 2-(2-Trifluoromethylphenyl)-5-methylpyridine (0.40 g, 1.68 mmol) and potassium permanganate (1.60 g, 10.1 mmol), in water (10 mL) was heated at reflux for 16 hours. The reaction was filtered hot through celite to remove the solids. Acetic acid was added to the colourless filtrate to yield a pH of 5 and the resulting suspension was extracted with CH2Cl2, washed with water (10 mL), dried, (MgSO4), and the solvent evaporated in vacuo to afford the title compound.

Workup

  1. temperatureat reflux for 16 hours
  2. filtrationThe reaction was filtered hot through celite
  3. customto remove the solids
  4. additionAcetic acid was added to the colourless filtrate
  5. customto yield a pH of 5
  6. extractionthe resulting suspension was extracted with CH2Cl2
  7. washwashed with water (10 mL)
  8. dry with materialdried, (MgSO4),
  9. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-3ec0301730bb4dd5829e024c0c345dbe
Source dataset
uspto-grants-1999_02
Patent number
US05872136

Reaction notes

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