2-Hydroxyquinoline → 1-(1,3-dioxolan-2-ylmethyl)quinolin-2(1H)-one

HRID 39689

Reaktionsgleichung

Reaktionsgleichung von HRID 39689
CN(C)C=O.[NH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]1=[O:16].[H-].[Na+].Br[CH2:20][CH:21]1[O:25][CH2:24][CH2:23][O:22]1>C(OCC)(=O)C.O>[O:22]1[CH2:23][CH2:24][O:25][CH:21]1[CH2:20][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]1=[O:16]

Komponenten

7

Edukt 4

HCID 60382-HydroxyquinolineHCID 6228DimethylformamideHCID 24758Sodium hydride3×HCID 780681,3-Dioxolane, 2-(bromomethyl)-3×

Produkt 1

HCID 593978641-(1,3-dioxolan-2-ylmethyl)quinolin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
52.5 °C

Versuchsvorschrift

To 11.5 mL of an N,N-dimethylformamide solution containing 1.15 g of quinolin-2(1H)-one, 0.35 g of 60% sodium hydride was added, and the mixture was stirred at 50 to 55° C. for 20 minutes. Thereto was added 0.90 mL of 2-bromomethyl-1,3-dioxolane, and the reaction mixture was stirred at 85 to 95° C. for 30 minutes. The reaction mixture was further added with 0.35 g of 60% sodium hydride and 0.90 mL of 2-bromomethyl-1,3-dioxolane, and stirred for 1 hour. The mixture was further added with 0.35 g of 60% sodium hydride and 0.90 mL of 2-bromomethyl-1,3-dioxolane, and stirred for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate 2:1] to obtain 0.89 g of a yellow oily substance, 1-(1,3-dioxolan-2-ylmethyl)quinolin-2(1H)-one.

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction mixture was stirred at 85 to 95° C. for 30 minutes
  3. stirringstirred for 1 hour
  4. stirringstirred for 1 hour and 30 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted twice with ethyl acetate
  8. washthe resultant solution was washed with a saturated sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customthe residue thus obtained
  12. customwas purified by silica gel column chromatography [eluent; hexane:ethyl acetate 2:1]

Quellen und Nachweise

ORD-Eintrag
ord-1482b7112e89491d827b644a08da0031
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524738B2

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