Potassium Permanganate → 6-fluoro-1-methyl-1H-indole-3-carboxylic acid

HRID 1372702

Reaction equation

HRID 1372702 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]=1

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 64981976-Fluoro-1-methyl-1H-indole-3-carbaldehyde

Product 1

HCID 178587926-fluoro-1-methyl-1H-indole-3-carboxylic acidYield 70.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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.

Workup

  1. stirringAfter stirring at room temperature for 10 hours
  2. filtrationthe reaction mixture was filtered through Celite
  3. distillationAfter the filtrate was distilled under reduced pressure under reduced pressure
  4. customThe crystals thus precipitated
  5. filtrationwere collected by filtration under reduced pressure
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-393e8cbf860d4fb4adbf3fc97834791b
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Linked notes

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