Water → 6-Bromo-8-fluoro-1-methyl-3,4-dihydroquinolin-2(1H)-one

HRID 530333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530333
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[NH:8][C:7](=[O:13])[CH2:6][CH2:5]2.[CH3:14]C(C)([O-])C.[K+].CI.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]([CH3:14])[C:7](=[O:13])[CH2:6][CH2:5]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 709774606-BROMO-8-FLUORO-3,4-DIHYDROQUINOLIN-2(1H)-ONE

Produkt 1

HCID 726988256-Bromo-8-fluoro-1-methyl-3,4-dihydroquinolin-2(1H)-oneAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 6-bromo-8-fluoro-3,4-dihydro-1H-quinolin-2-one (0.21 g, 0.86 mmol) in DMF (2 mL) was treated with potassium tert-butoxide (0.19 g, 1.72 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 30 min before methyl iodide (0.18 g, 1.29 mmol) was added. After stirring for 2 h, the reaction mixture was treated with water, extracted with EtOAc, washed with water and brine in sequence, and dried over anhy. Na2SO4. After removal of the solvents under reduced pressure, the crude product (0.18 g, 80% yield) was obtained as a white solid. MS: 258.0 (M+H)+.

Aufarbeitung

  1. additionwas added
  2. extractionextracted with EtOAc
  3. washwashed with water and brine in sequence
  4. customdried over anhy
  5. customAfter removal of the solvents under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d2c33c5ab35f418c9e7c0d6653b828ae
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353081B2

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