1,4-Dibromobutane → 7-(4-Bromobutoxy)-quinoline-2(1H)-one

HRID 1750080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750080
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.C([O-])([O-])=O.[K+].[K+]>CCO.O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 109757877-Hydroxycarbostyril

Produkt 1

HCID 107563157-(4-Bromobutoxy)-quinoline-2(1H)-oneAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of intermediate 14 (193 mg, 1.2 mmol), 1,4-dibromobutane (0.43 mL, 3.6 mmol) and anhydrous K2CO3 (166 mg, 1.2 mmol) was dissolved in EtOH and the solution was heated to reflux overnight. The solution was diluted with water and extracted with EtOAc. The combined organic layers was washed with saturated aq NaHCO3, brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with PE/EtOAc=2:1) to give 7-(4-bromobutoxy)quinolin-2(1H)-one (intermediate 15) (147 mg, 41%) as a yellow solid.

Aufarbeitung

  1. temperaturethe solution was heated
  2. temperatureto reflux overnight
  3. extractionextracted with EtOAc
  4. washThe combined organic layers was washed with saturated aq NaHCO3, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography on silica gel column (elution with PE/EtOAc=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-7a34e85f0b0448efa2fd470319653a82
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156822B2

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