Dimethyl Sulfate → 3,5-dimethoxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester

HRID 653143Notes

Reaction equation

HRID 653143 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=2)=[O:4].[C:23](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]2[C:12]([C:13]=1[O:14][CH3:23])=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=2)=[O:4]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 54696100Methyl 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylate

Product 1

HCID 545333813,5-dimethoxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 10.8 g (0.036 mole) of 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester [P. C. Unangst and M. E. Carethers, J. Heterocyclic Chem., 21, 709 (1984)] and 5.5 g (0.040 mole) of anhydrous potassium carbonate in 100 ml of acetone was treated with 3.7 ml (4.9 g; 0.039 mole) of dimethyl sulfate. The mixture was stirred and heated at reflux for 16 hours, cooled, and filtered. The filter cake was washed several times with fresh acetone, and the combined filtrates were evaporated (vacuum) to yield a crude residue of 3,5-dimethoxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester.

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe filter cake was washed several times with fresh acetone
  6. customthe combined filtrates were evaporated (vacuum)

Sources & evidence

ORD record
ord-14f36e025fe143e5b72819c043dae90b
Source dataset
uspto-grants-1987_06
Patent number
US04675332

Reaction notes

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