Potassium Permanganate → 6-fluoro-1-methyl-1H-indole-3-carboxylic acid
Reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:12]=[O:13])=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=[O:15].[K+]>CC(C)=O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]([OH:15])=[O:13])=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In acetone (200 ml) was dissolved 6-fluoro-1-methylindole-3-carbaldehyde (3.10 g, 17.5 mmol). To the resulting solution was added potassium permanganate (0.2M aqueous solution, 175 ml, 35.0 mmol) in portions under stirring at room temperature. After stirring at room temperature for 10 hours, the reaction mixture was filtered through Celite. After the filtrate was distilled under reduced pressure under reduced pressure, the residue was acidified with 1N HCl. The crystals thus precipitated were collected by filtration under reduced pressure, washed with water, and dried under reduced pressure to give 6-fluoro-1-methylindole-3-carboxylic acid (2.37 g, 70%) as a brown solid.