Quinoline → 11,12-Dihydro-11-phenylindolo[2,3-a]carbazole

HRID 408065

Reaktionsgleichung

Reaktionsgleichung von HRID 408065
[CH:1]1[C:6]2[N:7]=[C:8]3[C:20]4[C:12]([C:13]5[C:18]([N:19]=4)=[CH:17][CH:16]=[CH:15][CH:14]=5)=[CH:11][CH:10]=[C:9]3[C:5]=2[CH:4]=[CH:3][CH:2]=1.I[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].N1C2C(=CC=CC=2)C=CC=1>[Cu](I)I.ClCCl.O>[C:22]1([N:7]2[C:8]3[C:9](=[CH:10][CH:11]=[C:12]4[C:13]5[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=5[NH:19][C:20]4=3)[C:5]3[C:6]2=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

8

Edukt 4

HCID 7047QuinolineHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 21882147Indolo[2,3-a]carbazole

Produkt 1

HCID 5936587111,12-Dihydro-11-phenylindolo[2,3-a]carbazoleAusbeute 40,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
190 °C

Versuchsvorschrift

In a 1,000-ml three-necked flask that had been deaerated and filled with nitrogen were placed 26.0 g (101.4 millimoles) of indolo[2,3-a]carbazole, 122.7 g (601.4 millimoles) of iodobenzene, 54.7 g (287.2 millimoles) of copper iodide, 66.7 g (482.6 millimoles) of potassium carbonate, and 800 ml of quinoline and the mixture was stirred at 190° C. for 72 hours. The mixture was cooled to room temperature, 500 ml of water and 500 ml of dichloromethane were added, and the yellow crystals formed were filtered off. The filtrate was separated into an organic layer and an aqueous layer and the organic layer was washed three times with 500 ml of water. The organic layer was dried over magnesium sulfate, the magnesium sulfate was filtered off, and the solvent was stripped off under reduced pressure. The residue was purified by silica gel column chromatography to yield 13.7 g (41.2 millimoles, 40.6% yield) of 11-phenylindolo[2,3-a]carbazole as a white powder.

Aufarbeitung

  1. customIn a 1,000-ml three-necked flask that had been deaerated
  2. additionfilled with nitrogen
  3. temperatureThe mixture was cooled to room temperature
  4. customthe yellow crystals formed
  5. filtrationwere filtered off
  6. customThe filtrate was separated into an organic layer
  7. washan aqueous layer and the organic layer was washed three times with 500 ml of water
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationthe magnesium sulfate was filtered off
  10. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-428c48e6cbf44a4189124f3cccdbbc53
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08758904B2

Verknüpfte Notizen

Wird geladen…