Isatin → 3,3-Dimethoxy-1,3-dihydro-2H-indol-2-one

HRID 378690Notes

Reaction equation

HRID 378690 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)C(=O)[C:2]1=[O:3].[CH:12]([O:17][CH3:18])([O:15][CH3:16])OC>CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:18][O:17][C:12]1([O:15][CH3:16])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:1][C:2]1=[O:3]

Participants

5

Reactant 2

HCID 7054IsatinHCID 9005Trimethyl orthoformate

Product 1

HCID 154807453,3-Dimethoxy-1,3-dihydro-2H-indol-2-oneYield 76.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 887MethanolSolvent

Procedure

In 500 ml of methanol were dissolved 14.7 g of isatin and 10.6 g of trimethyl orthoformate, and 100 mg of p-toluenesulfonic acid was added thereto. The mixture was heated under reflux for 7 hours, followed by concentration. To the residue was added chloroform, and the mixture was washed with saturated aqueous sodium hydrogencarbonate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting crude product was purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=10/1) to give 14.7 g (76%) of the title compound as an oil.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 7 hours
  4. concentrationfollowed by concentration
  5. additionTo the residue was added chloroform
  6. washthe mixture was washed with saturated aqueous sodium hydrogencarbonate
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe resulting crude product was purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-c86667dbabab473fa4d1734f47d69e71
Source dataset
uspto-grants-2000_02
Patent number
US06031111

Reaction notes

Loading…