Potassium Permanganate → HCID 59425724, compound

HRID 907112Notes

Reaction equation

HRID 907112 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, was dissolved in acetone (98 mL). A solution of KMnO4 (655 mg, 4.15 mmol) in H2O (31 mL) was added. The reaction mixture was stirred at room temperature for 90 minutes. Another addition of KMnO4 (108 mg) in H2O (6 mL), followed by stirring for another 45 minutes was required to drive the reaction to completion. The reaction mixture was then quenched with 10% H2O2 (1.5 mL). The mixture was filtered through celite. The filtrate was stripped down under vacuum to roughly ⅓ of the volume. The residue was acidified with 6N HCl, and was extracted into ethyl acetate. The solids isolated from the ethyl acetate layer were 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 was then quenched with 10% H2O2 (1.5 mL)
  4. filtrationThe mixture was filtered through celite
  5. extractionwas extracted into ethyl acetate
  6. customThe solids isolated from the ethyl acetate layer
  7. customwere triturated with acetone

Sources & evidence

ORD record
ord-207537db73a84f478f42aa0bc0ef588e
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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