3-Bromoquinoline → 3-Methoxyquinoline

HRID 747335

Reaktionsgleichung

Reaktionsgleichung von HRID 747335
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:12][O-:13].[Na+]>CN(C=O)C>[CH3:12][O:13][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Komponenten

4

Edukt 2

HCID 214133-BromoquinolineHCID 10942334Sodium Methoxide

Produkt 1

HCID 5758073-MethoxyquinolineAusbeute 6,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 3-bromoquinoline (22.54 g, 108 mmol) in anhydrous DMF (110 mL) was treated with sodium methoxide (11.70 g, 217 mmol) and stirred at 80° C. for 16 hours. The reaction mixture was then concentrated and the residue taken up in ethyl acetate (300 mL) and water (60 mL). The organic phase was separated, washed with brine (2×60 mL), dried (MgSO4), filtered, concentrated and purified by column chromatography on silica gel (ethyl acetate/hexane; 1:3) to give 3-methoxyquinoline (1.06 g, 6%). 1H NMR (CDCl3) δ 3.95 (s, 3H), 7.38 (d, 1H, J=1.5 Hz), 7.54 (m, 2H), 7.72 (d, 1H, J=7.5 Hz), 8.04 (d, 1H, J=7.5 Hz), 8.67 (d, 1H, J=1.5 Hz).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated
  2. customThe organic phase was separated
  3. washwashed with brine (2×60 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography on silica gel (ethyl acetate/hexane; 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-eccdd586c3f04ad1b57a3171690ac408
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396840B2

Verknüpfte Notizen

Wird geladen…