2-Bromoanisole → N-(2-methoxyphenyl)-5-methoxyisatin

HRID 969932Notes

Reaction equation

HRID 969932 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[O:13].[H-].[Na+].Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24]>CN(C=O)C.[Cu](I)I>[CH3:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[C:6](=[O:13])[C:7]1=[O:12]

Participants

6

Reactant 3

HCID 113582-BromoanisoleHCID 24758Sodium hydrideHCID 383335-Methoxyisatin

Product 1

HCID 59017880N-(2-methoxyphenyl)-5-methoxyisatin

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

5-Methoxyisatin (2 g, 0.0113 mol) in anhydrous DMF (15 mL) was cooled in an ice-bath under a nitrogen atmosphere and treated with sodium hydride (0.54 g, 1.2 equivalents, 60% dispersion in mineral oil). The reaction was stirred at 0° C. for 0.5 hour and then 2-bromoanisole (1.4 mL, 1 equivalent) was added along with copper iodide (4.3 g, 2 equivalents). The reaction was heated in an oil-bath at 140° C. for 16 hours. The reaction was then cooled to room temperature and filtered. The filtrate was evaporated to dryness. The dark brown oily solid was used directly for the next reaction.

Workup

  1. temperatureThe reaction was heated in an oil-bath at 140° C. for 16 hours
  2. temperatureThe reaction was then cooled to room temperature
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customThe dark brown oily solid was used directly for the next reaction

Sources & evidence

ORD record
ord-da724738de504150b578b443c1ddfb3e
Source dataset
uspto-grants-2007_12
Patent number
US07309615B2

Reaction notes

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