Potassium Carbonate → 7-((4-(bromomethyl)cyclohexyl)methoxy)-3,4-dihydroquinolin-2(1H)-one

HRID 1750126

Reaktionsgleichung

Reaktionsgleichung von HRID 1750126
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[Br:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH:18]([CH2:21]Br)[CH2:17][CH2:16]1.C([O-])([O-])=O.[K+].[K+]>CCO.O>[Br:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][O:1][C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]3)=[CH:4][CH:3]=2)[CH2:17][CH2:16]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27857587-Hydroxy-3,4-dihydrocarbostyrilHCID 36135451,4-Bis(bromomethyl)cyclohexane

Produkt 1

HCID 665595897-((4-(bromomethyl)cyclohexyl)methoxy)-3,4-dihydroquinolin-2(1H)-oneAusbeute 30,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 7-hydroxy-3,4-dihydroquinolin-2(1H)-one (196 mg, 1.2 mmol), 1,4-bis(bromomethyl)cyclohexane (972 mg, 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 were washed with saturated aq NaHCO3, brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column to give 7-((4-(bromomethyl)cyclohexyl)methoxy)-3,4-dihydroquinolin-2(1H)-one (intermediate 49) (130 mg, 30%) as a white solid.

Aufarbeitung

  1. temperaturethe solution was heated
  2. temperatureto reflux overnight
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were 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

Quellen und Nachweise

ORD-Eintrag
ord-6150a2e0a4d2410595df8590dfb92250
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156822B2

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