Sodium Hydroxide → 3-Nitroquinolin-6-ol

HRID 1043783

Reaktionsgleichung

Reaktionsgleichung von HRID 1043783
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6]2.[OH-].[Na+]>Br>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6]2

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 15193946-Methoxy-3-nitroquinoline

Produkt 1

HCID 595075803-Nitroquinolin-6-olAusbeute 78,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 260Hydrogen BromideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

6-Methoxy-3-nitroquinoline (Magnus, P. et al., J. Am. Chem. Soc. 119, 5591, 1997; 100 mg, 0.49 mmol) was dissolved in hydrogen bromide solution (47% aq, 2.5 mL, 0.2 M), heated and stirred at 120° C. for 16 hours. The reaction mixture was cooled to room temperature, neutralized with 6N NaOH, then extracted with EtOAc (150 mL). The organic layer was dried over Na2SO4 and purified by flash chromatography (SiO2, 40-50% EtOAc/hexanes), obtaining 73 mg (78%) of 6-hydroxy-3-nitroquinoline. LC/MS (m/z): 190.9 (MH+), Rt 1.97 minutes.

Aufarbeitung

  1. temperatureheated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with EtOAc (150 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. custompurified by flash chromatography (SiO2, 40-50% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b540758489894aadb3813cec2b442019
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563549B2

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