Water → 5-fluoropyridine-2-carboxylic Acid

HRID 586802

Reaction equation

HRID 586802 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.[Mn]([O-])(=O)(=O)=[O:10].[K+].[OH2:15]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:15])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 27628635-Fluoro-2-methylpyridine

Product 1

HCID 27628765-fluoropyridine-2-carboxylic AcidYield 28%

Procedure

To water (100 ml) were added 5-fluoro-2-methylpyridine (J. Med. Chem., 32, 1970(1989): 2.2 g, 20 mmol) and potassium permanganate (19.1 g, 120 mmol), and heated under reflux for 4 hours. The reaction mixture was filtrated and the filtrate was concentrated, acidified with KHSO4, extracted with ethyl acetate and the extract was dried over Na2SO4. The solvent was evaporated to give the title compound (0.80 g; 28%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. filtrationThe reaction mixture was filtrated
  4. concentrationthe filtrate was concentrated
  5. extractionextracted with ethyl acetate
  6. dry with materialthe extract was dried over Na2SO4
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-0679ce60ed2046d98a2dfdf025d884e4
Source dataset
uspto-grants-2005_08
Patent number
US06936736B2

Linked notes

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