4-Fluorophenol → 2-(4-Fluorophenoxy)nicotinic acid

HRID 350974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350974
C([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1Cl)C.[F:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[OH-].[Li+].O>[F:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:6]2[N:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([OH:3])=[O:12])=[CH:16][CH:15]=1

Komponenten

7

Edukt 3

HCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 2796614Ethyl chloronicotinate

Produkt 1

HCID 6051232-(4-Fluorophenoxy)nicotinic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3939Lithium HydroxideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-Chloro-nicotinic acid ethyl ester, 4-fluoro-phenol, and cesium carbonate were mixed in anhydrous dioxane and the resulting slurry heated to reflux for about 16 h. In a separate flask, lithium hydroxide was dissolved in water with warming and then added to the refluxing mixture, which was heated for an additional 4 h. The mixture was cooled to ambient temperature and concentrated in vacuo to remove the dioxane. Concentrated hydrochloric acid was added dropwise until the pH=3. The acidified solution was then extracted with ethyl acetate to yield crude product, which was recrystallized from ethyl acetate to yield the purified title compound (10.8 g).

Aufarbeitung

  1. temperaturethe resulting slurry heated
  2. temperatureto reflux for about 16 h
  3. temperaturewith warming
  4. additionadded to the refluxing mixture, which
  5. temperaturewas heated for an additional 4 h
  6. concentrationconcentrated in vacuo
  7. customto remove the dioxane
  8. additionConcentrated hydrochloric acid was added dropwise until the pH=3
  9. extractionThe acidified solution was then extracted with ethyl acetate
  10. customto yield crude product, which
  11. customwas recrystallized from ethyl acetate
  12. customto yield the
  13. custompurified title compound (10.8 g)

Quellen und Nachweise

ORD-Eintrag
ord-2b937f01fac34886af3fdecf06c3e956
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183293B2

Notizen zur Reaktion

Wird geladen…