Water → 5-fluoropyridine-2-carboxylic Acid

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

Reactant 3

HCID 962Water

HCID 516875Potassium Permanganate

HCID 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%).