Dimethylformamide → 3-Chloroquinoline-7-carbonitrile

HRID 1465739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1465739
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([Cl:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:13]([Cu])#[N:14].CN(C=O)C>C(Cl)Cl>[Cl:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[C:2]([C:13]#[N:14])[CH:11]=2

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 533932407-Bromo-3-chloroquinolineHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 895252713-Chloroquinoline-7-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a flask containing a stir bar was added 7-Bromo-3-chloroquinoline (1.0 g, 4.1 mmol), CuCN (0.55 g, 6.2 mmol), and DMF (25 mL). The mixture was then refluxed at 150° C. overnight. When the reaction was complete, as evidenced by LC analysis, the reaction flask was taken out of the oil bath and cooled to room temperature. To the reaction mixture was then poured DCM (20 mL) and a precipitate formed immediately, which was filtered off. The crude product was adsorbed onto silica gel and purified by silica gel column chromatography (Hexanes:DCM→1:1) to provide the title product.

Aufarbeitung

  1. additionTo a flask containing a stir bar
  2. temperaturecooled to room temperature
  3. filtrationwhich was filtered off
  4. custompurified by silica gel column chromatography (Hexanes:DCM→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-4e4be921e4394c1eb71db861ed04959f
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999991B2

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