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4-Bromo-2,6-dimethylquinoline → 4-Cyano-2,6-dimethylquinoline

HRID 1581453
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1581453
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[C:14]([Cu])#[N:15]>CN(C=O)C>[C:14]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1)#[N:15]
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Komponenten

4

Edukt 2

HCID 149913604-Bromo-2,6-dimethylquinolineHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 149913674-Cyano-2,6-dimethylquinolineAusbeute 55,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

First, 4-bromo-2,6-dimethylquinoline (5.0 g) and CuCN (4.82 g) were added to DMF (70 ml) and were allowed to react for 6 hours at a temperature of 140° C. Ice was poured to the reaction solution and the produced precipitate was removed through filtering. The filtrate was extracted using ethyl acetate, the solvent was removed under reduced pressure, and the residue was purified through column chromatography (silica gel, hexane/ethyl acetate=4/1) to obtain 4-cyano-2,6-dimethylquinoline (2.14 g) represented by the following chemical formula (47).

Aufarbeitung

  1. customto react for 6 hours at a temperature of 140° C
  2. additionIce was poured to the reaction solution
  3. customthe produced precipitate was removed
  4. filtrationthrough filtering
  5. extractionThe filtrate was extracted
  6. customthe solvent was removed under reduced pressure
  7. customthe residue was purified through column chromatography (silica gel, hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-ace30e94cb794f45b8109612a8052ec2
Quelldatensatz
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06730418B2

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