Water → 5-fluoropyridine-2-carboxylic Acid

HRID 1934360

Reaction equation

HRID 1934360 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 sol vent 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 sol vent was evaporated

Sources & evidence

ORD record
ord-159807f999c849d1a9a4d7e5ef5a5db9
Source dataset
uspto-grants-2002_05
Patent number
US06384033B1

Linked notes

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