Benzyl Bromide → 5-Benzyloxy-8-nitro-quinoline

HRID 513798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 513798
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[N+:15]([C:18]1[C:27]2[N:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]([OH:28])=[CH:20][CH:19]=1)([O-:17])=[O:16]>CN(C=O)C.O>[CH2:2]([O:28][C:21]1[CH:20]=[CH:19][C:18]([N+:15]([O-:17])=[O:16])=[C:27]2[C:22]=1[CH:23]=[CH:24][CH:25]=[N:26]2)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 52973548-Nitroquinolin-5-ol

Produkt 1

HCID 681832585-Benzyloxy-8-nitro-quinolineAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Bromomethyl-benzene (424 μl, 3.57 mmol) and K2CO3 (493 mg, 3.57 mmol) were added to a solution of 8-nitro-quinolin-5-ol 563 (566 mg, 2.98 mmol) in DMF (5 ml) and the mixture was heated at 90° C. for 6 h. After cooling, the mixture was diluted with water (25 ml) and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine (25 ml), dried (Na2SO4) and concentrated in vacuo to give the title compound (572 mg, 69%) which was used in the next step without further purification.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe aqueous phase was extracted with EtOAc
  3. washThe combined organic phases were washed with brine (25 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b9066617c1b1418c863d1d45f1efddac
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102688B2

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