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

HRID 1986714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1986714
[F: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]([F: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 136907656-Fluoro-3,4-dihydroquinolin-2(1H)-one

Produkt 1

HCID 179561031-(3-Chloropropyl)-6-fluoro-3,4-dihydro-1H-quinolin-2-oneAusbeute 73,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A reaction flask was charged with 6-fluoro-3,4-dihydro-1H-quinolin-2-one (0.180 g, 1.09 mmol) in dry DMF (2 mL) under Argon. NaH (60% in oil, 0.048 g, 1.20 mmol) was added and the mixture was stirred at rt for 0.5 h. Then 1-bromo-3-chloropropane (0.180 g, 1.14 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 product was purified by flash CC (SiO2; DCM) to give the title compound (92LH79) (0.193 g, 73%). 1H NMR (CDCl3) d 7.02-6.88 (m, 3H), 4.09-4.05 (m, 2H), 3.61 (t, J=6.3 Hz, CH2), 2.87 (t, J=6.7 Hz, Ch2), 2.65-2.61 (m, 2H), 2.16-2.09 (m, 2H); 13C NMR (CDCl3) d 169.8, 158.4 (J=242.9 Hz), 135.7 (J=2.7 Hz), 128.5 (J=7.7 Hz), 115.7 (J=8.1 Hz), 115.1 (J=22.7), 113.8 (J=22.3 Hz), 42.6, 40.3, 31.5, 30.1, 25.5.

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 product was purified by flash CC (SiO2; DCM)

Quellen und Nachweise

ORD-Eintrag
ord-87feec70c21348d1922716903abc5fd6
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550459B2

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