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

HRID 506431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506431
[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]

Komponenten

6

Edukt 3

HCID 113582-BromoanisoleHCID 24758Sodium hydrideHCID 383335-Methoxyisatin

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-67d722f30b5e4989bc0cb65ab7cdac93
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07785904B2

Notizen zur Reaktion

Wird geladen…