Potassium Permanganate → HCID 59425724, compound

HRID 252504Notes

Reaction equation

HRID 252504 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:16]=[O:17])=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:7][CH:6]=1)=[O:4].[O-:18][Mn](=O)(=O)=O.[K+]>CC(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:16]([OH:18])=[O:17])=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 516875Potassium Permanganate2×HCID 59425156Methyl 1-ethyl-3-formyl-1H-indole-6-carboxylate

Product 1

HCID 59425724HCID 59425724, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

1-Ethyl-3-formyl-1H-indole-6-carboxylic acid methyl ester (800 mg, 3.5 mmol), prepared as shown in example 1P, step A, is dissolved in acetone (98 mL). A solution of KMnO4 (655 mg, 4.15 mmol) in H2O (31 mL) is added. The reaction mixture is stirred at room temperature for 90 minutes. Another addition of KMnO4 (108 mg) in H2O (6 mL), followed by stirring for another 45 minutes is required to drive the reaction to completion. The reaction mixture is then quenched with 10% H2O2 (1.5 mL). The mixture is filtered through celite. The filtrate is stripped down under vacuum to roughly ⅓ of the volume. The residue is acidified with 6N HCl, and is extracted into ethyl acetate. The solids isolated from the ethyl acetate layer are triturated with acetone to yield 1-ethyl-1H-indole-3,6-dicarboxylic acid 6-methyl ester (696 mg, 79%) as a light orange solid.

Workup

  1. stirringby stirring for another 45 minutes
  2. customthe reaction to completion
  3. customThe reaction mixture is then quenched with 10% H2O2 (1.5 mL)
  4. filtrationThe mixture is filtered through celite
  5. extractionis extracted into ethyl acetate
  6. customThe solids isolated from the ethyl acetate layer
  7. customare triturated with acetone

Sources & evidence

ORD record
ord-26e6c966e2104b02b004fe2b38a8d990
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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