Potassium Cyanide → [7-Fluoro-2-(methyloxy)-8-quinolinyl]acetonitrile

HRID 527946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527946
Br[CH2:2][C:3]1[C:4]([F:15])=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13][CH3:14])[CH:9]=[CH:8]2.[C-:16]#[N:17].[K+]>CN(C=O)C>[F:15][C:4]1[C:3]([CH2:2][C:16]#[N:17])=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([O:13][CH3:14])=[N:11]2)=[CH:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 9032Potassium CyanideHCID 667376508-(Bromomethyl)-7-fluoro-2-(methyloxy)quinoline

Produkt 1

HCID 67130956[7-Fluoro-2-(methyloxy)-8-quinolinyl]acetonitrileAusbeute 100,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 8-bromomethyl-7-fluoro-2-methoxy-quinoline (20.0 g, 74 mmol; prepared as in WO 2007/081597) in DMF (530 mL) was added KCN (22.1 g, 339 mmol) and the mixture was stirred at 70° C. overnight. The mixture was concentrated, water and EA were added and the aq. layer was extracted with EA. The combined org layers were washed with brine, dried over MgSO4 and concentrated to afford the title intermediate as a beige solid (16.13 g, 100% yield).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. additionwater and EA were added
  3. extractionthe aq. layer was extracted with EA
  4. washThe combined org layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cd50df7b1f074bb7abb3cb0bb227f483
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346804B2

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