Sodium Hydroxide → 8-Quinolinamine, 6-bromo-

HRID 992060

Reaktionsgleichung

Reaktionsgleichung von HRID 992060
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-])=O)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[OH-].[Na+]>CCO.CC(O)=O.O.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH2:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 1104636-Bromo-8-nitroquinoline

Produkt 1

HCID 936378-Quinolinamine, 6-bromo-Ausbeute 905,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 86584229Acetic acid ethanol waterLösungsmittel

Versuchsvorschrift

To a solution of 6-bromo-8-nitro-quinoline (4 g, 1.58 mmol) in EtOH/HOAc/H2O (50 mL/50 mL/25 mL) was added iron metal (3.18 g, 5.69 mmol). The resulting solution was heated at reflux for 3 hours. The cooled reaction mixture was neutralized with 2.5 N NaOH, filtered through celite to remove iron solids and washed with EtOAc. The eluent was extracted into EtOAc (3×200 mL), combined, dried over Na2SO4 and concentrated. The resulting oil was purified by column chromatography (40% EtOAc/hexanes) affording 3.19 g (91%) of a yellow solid: mp 142-145° C.

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 3 hours
  3. customThe cooled reaction mixture
  4. filtrationfiltered through celite
  5. customto remove iron solids
  6. washwashed with EtOAc
  7. extractionThe eluent was extracted into EtOAc (3×200 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe resulting oil was purified by column chromatography (40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f82f16457eae4002a068ded2e6745ae0
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06465482B2

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