3-Bromopyridine → 2-Methoxy-6-(3-pyridyl)quinoline

HRID 986001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 986001
C([Li])(C)(C)C.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[CH3:13][O:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20](Br)[CH:21]=2)[N:16]=1.[Cl-].[NH4+]>CCCCC.C1COCC1.[Cl-].[Zn+2].[Cl-]>[CH3:13][O:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:7]3[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=3)[CH:21]=2)[N:16]=1

Komponenten

8

Edukt 4

HCID 122863-BromopyridineHCID 25517Ammonium ChlorideHCID 106575386-Bromo-2-methoxyquinolineHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 142209722-Methoxy-6-(3-pyridyl)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 8003PentaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

t-Butyl lithium (7.7 cm3 of a 2.6M solution in pentane) was added dropwise over 5 minutes to a stirred solution of 3-bromopyridine (1.44 cm3) in THF (25 cm3) at -100° under nitrogen. After stirring for 10 minutes a solution of anhydrous zinc chloride (2.05 g) in THF (20 cm3) was added slowly and the mixture was allowed to warm to room temperature over 1 hour. A solution of 2-methoxy-6-bromoquinoline (2.38 g) and tetrakis-(triphenylphosphine)palladium(O) (0.08 g) in THF (10 cm3) was added and the mixture was heated under reflux for 9 hours. Ammonium chloride solution (20 cm3) was then added, the mixture was concentrated in vacuo, and the aqueous phase extracted with chloroform (3×50 cm3). The dried (MgSO4) extracts were evaporated in vacuo to give a solid which was chromatographed on silica (Merck "MK. 60.9385") eluting with ethyl acetate:hexane, 1:1, to afford a residue which was recrystallised from petroleum ether (b.p. 60°-80°)-ether to afford 2-methoxy-6-(3-pyridyl)quinoline, m.p. 89°-91°, (0.35 g).

Aufarbeitung

  1. additionwas added slowly
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 9 hours
  4. concentrationthe mixture was concentrated in vacuo
  5. extractionthe aqueous phase extracted with chloroform (3×50 cm3)
  6. dry with materialThe dried (MgSO4) extracts
  7. customwere evaporated in vacuo
  8. customto give a solid which
  9. customwas chromatographed on silica (Merck "MK. 60.9385")
  10. washeluting with ethyl acetate
  11. customhexane, 1:1, to afford a residue which
  12. customwas recrystallised from petroleum ether (b.p. 60°-80°)-ether

Quellen und Nachweise

ORD-Eintrag
ord-9cf0f4eedfa14c4abbb211316b2ed066
Quelldatensatz
uspto-grants-1987_12
Patentnummer
US04710507

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