Isatin → 1-(4-Methoxyphenyl)indoline-2,3-dione

HRID 506429Notes

Reaction equation

HRID 506429 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[H-].[Na+].Br[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1>CN(C=O)C.C(OCC)(=O)C.[Cu](I)I>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([N:1]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4](=[O:5])[C:2]2=[O:3])=[CH:16][CH:17]=1

Participants

7

Reactant 3

HCID 7054IsatinHCID 77304-BromoanisoleHCID 24758Sodium hydride

Product 1

HCID 139250941-(4-Methoxyphenyl)indoline-2,3-dione

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of isatin (2.5 g, 0.017 mol) in anhydrous DMF (50 mL) was cooled to 0° C. in an ice-bath and treated with sodium hydride (0.5 g, 1.2 equivalents). A purple solution was formed which was stirred at 0° C. for 30 minutes and then warmed to room temperature. To this solution was added 4-bromoanisole (2.13 mL, 1 equivalent) followed by copper iodide (6.46 g, 2 equivalents). The reaction was heated in an oil-bath at 145° C. for 6-7 hours. The reaction was then cooled to room temperature, diluted with an equal volume of ethyl acetate and filtered. The filtrate was evaporated to dryness. The crude product, which was obtained as a dark brown solid was used as such for the next reaction.

Workup

  1. customA purple solution was formed which
  2. temperaturewarmed to room temperature
  3. temperatureThe reaction was heated in an oil-bath at 145° C. for 6-7 hours
  4. temperatureThe reaction was then cooled to room temperature
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-658a8f8643c94eacbbd5e4d286e934a1
Source dataset
uspto-grants-2010_08
Patent number
US07785904B2

Reaction notes

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