1-Bromo-3-chloropropane → 1-(3-Chloropropyl)-6-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 1191379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191379
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][Cl:19]>CN(C=O)C>[Cl:19][CH2:18][CH2:17][CH2:16][N:8]1[C:9]2[C:4](=[CH:3][C:2]([CH3:1])=[CH:11][CH:10]=2)[CH2:5][CH2:6][C:7]1=[O:12]

Komponenten

5

Edukt 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 152705756-Methyl-3,4-dihydroquinolin-2(1H)-one

Produkt 1

HCID 179560711-(3-Chloropropyl)-6-methyl-3,4-dihydro-1H-quinolin-2-oneAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A reaction flask was charged with 6-methyl-3,4-dihydro-1H-quinolin-2-one (107LH05) (0.300 g, 1.26 mmol) in dry DMF (5 mL) under Argon. NaH (60% in oil, 0.055 g, 1.38 mmol) was added and the mixture was stirred at rt for 1 h. Then 1-bromo-3-chloropropane (0.198 g, 1.24 mmol) was added followed by stirring at rt for 20 h. The reaction mixture was quenched with water, and the product extracted into EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude product was purified by flash CC (SiO2; DCM) to give the crude title compound (107LH14) (0.257 g).

Aufarbeitung

  1. stirringby stirring at rt for 20 h
  2. customThe reaction mixture was quenched with water
  3. extractionthe product extracted into EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash CC (SiO2; DCM)

Quellen und Nachweise

ORD-Eintrag
ord-014b6931c6d74e4087a43e314a8ee713
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680115B2

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