2-Hydroxyquinoline → 1-(3-chloropropyl)quinolin-2(1H)-one

HRID 1191383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191383
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]1=[O:11].CN(C=O)C.[H-].[Na+].Br[CH2:20][CH2:21][CH2:22][Cl:23]>CCOC(C)=O>[Cl:23][CH2:22][CH2:21][CH2:20][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]1=[O:11]

Komponenten

6

Edukt 4

HCID 60382-HydroxyquinolineHCID 6228DimethylformamideHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydride

Produkt 1

HCID 193797261-(3-chloropropyl)quinolin-2(1H)-oneAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 7 mL vial was charged with 1H-quinolin-2-one (0.62 g, 4.2 mmol), 4 mL dry DMF and NaH (60% in oil, 0.200 g, 5.1 mmol). The mixture was stirred under a N2 atmosphere at rt for 45 min, and thereafter 1-bromo-3-chloropropane (0.42 mL, 4.2 mmol) was added and the reaction was stirred at rt overnight. The reaction was diluted with EtOAc (50 mL) and washed with water (15 mL). The water phase was extracted with EtOAc (25 mL) and the combined organic phase was dried (Na2SO4), filtered, concentrated under reduced pressure and the residue was purified by flash chromatography (SiO2; CH2Cl2) to yield the title compound (0.38 g, 41%), containing 15% of 1-(3-bromopropyl)-1H-quinolin-2-one. 1H NMR (CD3OD) δ 7.90 (d, J=9.4 Hz, 1H), 7.73-7.57 (m, 3H), 7.34-7.28 (m, 1H), 6.66 (d, J=9.4 Hz), 4.46 (t, J=7.4 Hz, 2H), 3.71 (t, J=6.4 Hz, 2H), 2.21-2.02 (m, 2H); 13C NMR (CD3OD) δ 163.2, 140.7, 138.8, 131.3, 129.3, 122.8, 121.4, 120.2, 114.4, 42.18, 40.2, 30.5.

Aufarbeitung

  1. stirringthe reaction was stirred at rt overnight
  2. washwashed with water (15 mL)
  3. extractionThe water phase was extracted with EtOAc (25 mL)
  4. dry with materialthe combined organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by flash chromatography (SiO2; CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-189add6e824f46e7a41d8ac326efabd2
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680115B2

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