Isatin → HCID 15480746, compound

HRID 365980Notes

Reaction equation

HRID 365980 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:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])OCC>C(O)C.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>[CH2:20]([O:19][C:12]1([O:16][CH2:17][CH3:18])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:1][C:2]1=[O:3])[CH3:21]

Participants

5

Reactant 2

HCID 7054IsatinHCID 31214Ethyl orthoformate

Product 1

HCID 15480746HCID 15480746, compoundYield 128.9%

Reagents, catalysts & solvents 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 702EthanolSolvent

Procedure

In 500 ml of ethanol were dissolved 14.7 g of isatin and 10.6 g of triethyl orthoformate, and 100 mg of camphorsulfonic acid was added thereto. The mixture was heated under reflux for 12 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 (chloroform/ethyl acetate=10/1) to give 20.4 g (92%) of the title compound as an oil.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 12 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 (chloroform/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-c0bbc14b8a9c4be88fe9f26218f74e9d
Source dataset
uspto-grants-2000_10
Patent number
US06127544

Reaction notes

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