Potassium Permanganate → 2-Chloro-1-[2-(3-methoxy-propoxy)-phenyl]-1h-indole-3-carboxylic acid

HRID 1510074Notes

Reaction equation

HRID 1510074 reaction equation
[Cl:1][C:2]1[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH2:20][CH2:21][CH2:22][O:23][CH3:24])[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.P([O-])([O-])(O)=[O:26].[Na+].[Na+].P([O-])(O)(O)=O.[K+].[Mn]([O-])(=O)(=O)=O.[K+]>CC(C)=O.O.CC(=O)OCC>[Cl:1][C:2]1[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH2:20][CH2:21][CH2:22][O:23][CH3:24])[C:4]2[C:9]([C:10]=1[C:11]([OH:26])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

7

Reactant 3

HCID 516875Potassium PermanganateHCID 71312623Disodium hydrogenphosphate potassium dihydrogenphosphateHCID 872052752-Chloro-1-[2-(3-methoxy-propoxy)-phenyl]-1h-indole-3-carbaldehyde

Product 1

HCID 669203792-Chloro-1-[2-(3-methoxy-propoxy)-phenyl]-1h-indole-3-carboxylic acid

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To the compound of step 4 (100 mg, 2914 μmol) in a mixture of acetone (2.8 ml), water (1.36 ml) and a disodium hydrogenphosphate/potassium dihydrogenphosphate buffer solution (2.0 ml; pH 7.0) was added with stirring at room temperature potassium permanganate (90.0 mg, 570 μmol) in small portions. After stirring at room temperature for 3 days, the mixture was diluted with water and EA was added. The organic layer was separated, dried over sodium sulfate, filtered, and evaporated. The residue was purified by silica gel chromatography (EA/HEP 4:1). 50 mg of the title compound were obtained.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by silica gel chromatography (EA/HEP 4:1)

Sources & evidence

ORD record
ord-da6d9b5c7ea24ee8bfbff6e55849731a
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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