Potassium Permanganate → 4-Fluoro-1-methyl-1h-indole-3-carboxylic acid

HRID 1372711Notes

Reaction equation

HRID 1372711 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:12]=[O:13])=[CH:5][N:6]2[CH3:11].[Mn]([O-])(=O)(=O)=[O:15].[K+]>CC(C)=O>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:12]([OH:15])=[O:13])=[CH:5][N:6]2[CH3:11]

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 221389944-fluoro-1-methyl-1H-indole-3-carbaldehyde

Product 1

HCID 183852904-Fluoro-1-methyl-1h-indole-3-carboxylic acidYield 58%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In acetone (95 ml) was dissolved 4-fluoro-1-methylindole-3-carbaldehyde (1.43 g, 8.08 mmol), followed by the addition of potassium permanganate (a 0.2M aqueous solution, 62.0 ml, 12.4 mmol) in portions at room temperature. After the reaction mixture was stirred at room temperature for 16 hours, the precipitate was filtered off through Celite. The filtrate was distilled under reduced pressure to remove the solvent. 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 4-fluoro-1-methylindole-3-carboxylic acid (0.91 g, 58%) as a brown solid.

Workup

  1. filtrationthe precipitate was filtered off through Celite
  2. distillationThe filtrate was distilled under reduced pressure
  3. customto remove the solvent
  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-a94b44e6e76547e1a7bd7ed5f8469655
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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