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

HRID 6603

Reaction equation

HRID 6603 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:16]=[C:17]([CH:21]2[O:25][CH2:24][CH2:23][O:22]2)[CH:18]=[CH:19][CH:20]=1.CO>CN(C=O)C.C(Cl)(Cl)Cl.[Cu]I>[O:22]1[CH:23]=[CH:24][O:25][CH:21]1[C:17]1[CH:16]=[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:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 7054IsatinHCID 24758Sodium hydrideHCID 873062-(3-Bromophenyl)-1,3-dioxolane

Product 1

HCID 21972258N-[3-(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

Conditions

Temperature
0 °C

Procedure

Isatin (3.2 g, 0.0218 mol) was dissolved in anhydrous DMF (75 mL) and cooled in an ice-bath under a nitrogen atmosphere. To this cold solution, sodium hydride (0.575 g, 0.0239 mol) was added and the reaction was stirred at 0° C. for 1.5 hours. This solution was then treated with 2-(3-bromophenyl)-1,3-dioxolane (5 g, 1 equivalent) followed by CuI (8.3 g, 2 equivalents). The resulting suspension was heated in an oil-bath under nitrogen at 130–140° C. for 16 hours. It was then cooled to room temperature and diluted with an equal volume of chloroform. This suspension was filtered and the filtrate was concentrated under reduced pressure. A viscous brown oil was recovered which was suspended in xylenes (150 mL) wand evaporated to dryness. The residue was used as such for the next reaction. TLC (5% methanol in chloroform) showed clean conversion; Rf (product)=0.86.

Workup

  1. temperaturecooled in an ice-bath under a nitrogen atmosphere
  2. temperatureThe resulting suspension was heated in an oil-bath under nitrogen at 130–140° C. for 16 hours
  3. temperatureIt was then cooled to room temperature
  4. filtrationThis suspension was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customA viscous brown oil was recovered which
  7. customwand evaporated to dryness
  8. customsuch for the next reaction

Sources & evidence

ORD record
ord-4307fdaae0dc4d9bb621a9607ef82b36
Source dataset
uspto-grants-2006_08
Patent number
US07083986B2

Linked notes

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