Sodium Bicarbonate → (7-Fluoro-2-methoxy-quinolin-8-yl)-methanol

HRID 1801463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1801463
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([O-])(O)=[O:17].[Na+]>CC(C)=O.O>[F:15][C:4]1[C:3]([CH2:2][OH: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

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 667376508-(Bromomethyl)-7-fluoro-2-(methyloxy)quinoline

Produkt 1

HCID 66737655(7-Fluoro-2-methoxy-quinolin-8-yl)-methanolAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A suspension of 8-bromomethyl-7-fluoro-2-methoxy-quinoline (25 g, 92.56 mmol) in acetone (360 mL) and water (460 mL) was treated with NaHCO3 (12.74 g, 151.64 mmol, 1.6 eq). The mixture was heated to reflux overnight. After cooling, the volatiles were removed in vacuo and the residue was partitioned between EA (300 mL) and water (100 mL). The aq. layer was extracted once with EA (250 mL) and the combined org. layers were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by CC (Hept-EA 3:1) to afford the title alcohol as a yellowish solid (14.04 g).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureAfter cooling
  4. customthe volatiles were removed in vacuo
  5. customthe residue was partitioned between EA (300 mL) and water (100 mL)
  6. extractionThe aq. layer was extracted once with EA (250 mL)
  7. washlayers were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to dryness
  11. customThe residue was purified by CC (Hept-EA 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-a03dacb1f55842778ada5a0aedfead45
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349828B2

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