Potassium Iodide → HCID 21194466, compound

HRID 565063Notes

Reaction equation

HRID 565063 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:12])[CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[C:3]1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[C:18](=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:12])[CH:7]=[CH:8][C:9]=2[O:11][CH3:18])[CH:4]=[C:3]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 12050031HCID 12050031, compound

Product 1

HCID 21194466HCID 21194466, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.50 g (15.5 mmol) of ethyl 1,4-dimethyl-7-hydroxy-2-indolecarboxylate, 4.14 g (30.0 mmol) of potassium carbonate, 4.26 g (30.0 mmol) of potassium iodide and dimethylformamide was stirred at room temperature for 2 hours. The reaction mixture was poured onto ice water followed by extraction with ethyl acetate. The extract was washed with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 3.21 g of ethyl 1,4-dimethyl-7-methoxy-2-indolecarboxylate.

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a5e21c51ecac4ae293aa0df02a694388
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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