Water → HCID 19092861, compound

HRID 487662Notes

Reaction equation

HRID 487662 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](I)[CH3:8].[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[NH:17][C:16]([C:23]([OH:25])=[O:24])=[C:15]2[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=1.O>CN(C)C=O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[NH:17][C:16]([C:23]([O:25][CH2:7][CH3:8])=[O:24])=[C:15]2[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 19092862HCID 19092862, compound

Product 1

HCID 19092861HCID 19092861, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.139 g) and ethyl iodide (0.13 ml) were added to a solution of 5,6-dimethoxy-3-(3,4-dimethoxyphenyl)indole-2-carboxylic acid (0.3 g) in N,N-dimethylformamide (5 ml). The mixture was stirred for 3 hours at room temperature, poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The precipitated crystals were collected by filtration and recrystallized from ethanol to give ethyl 5,6-dimethoxy-3-(3,4-dimethoxyphenyl)indole-2-carboxylate (0.272 g, 84%) as pale red prisms.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. filtrationThe precipitated crystals were collected by filtration
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-050e1c2f9dbb4293995f7505d3aba43a
Source dataset
uspto-grants-1994_03
Patent number
US05296499

Reaction notes

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