Methanol → N-[4-(1,3-dioxolyl)phenyl]isatin

HRID 6607

Reaction equation

HRID 6607 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+].[CH3:14][OH:15]>CN(C=O)C.C(Cl)(Cl)Cl.[Cu]I>[O:15]1[CH:4]=[CH:2][O:3][CH:14]1[C:6]1[CH:11]=[CH:10][C:9]([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:8][CH:7]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 7054IsatinHCID 24758Sodium hydride

Product 1

HCID 22016430N-[4-(1,3-dioxolyl)phenyl]isatin

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Isatin (1.88 g, 0.0128 mol) in anhydrous DMF (100 mL) was cooled in an ice-bath under nitrogen and treated with sodium hydride (0.3 g, 1 equivalent). The reaction was warmed to room temperature and stirred for 1 hour. It was then treated with 2-(4-bromophenyl)-1,3-dioxalane (2.83 g, 0.0124 mol) followed by CuI (4.71 g, 2 equivalents). This suspension was heated in an oil-bath at 135° C. under nitrogen for 16 hours. It was then cooled to room temperature and diluted with an equal volume of chloroform. The resulting suspension was filtered and the filtrate was concentrated under reduced pressure. The residue was suspended in xylenes (100 mL) and evaporated to dryness. A thick, viscous oil was recovered which was used as such for the next reaction. TLC (5% methanol in chloroform) showed clean conversion, Rf (product)=0.91.

Workup

  1. temperatureThis suspension was heated in an oil-bath at 135° C. under nitrogen for 16 hours
  2. temperatureIt was then cooled to room temperature
  3. filtrationThe resulting suspension was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customevaporated to dryness
  6. customA thick, viscous oil was recovered which
  7. customsuch for the next reaction

Sources & evidence

ORD record
ord-bee7a5bb378040a9ab29ac748036e612
Source dataset
uspto-grants-2006_08
Patent number
US07083986B2

Linked notes

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