Water → 6-Bromo-8-chloro-1-methyl-1,2,3,4-tetrahydroquinolin-2-one

HRID 1774843

Reaktionsgleichung

Reaktionsgleichung von HRID 1774843
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl: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]([Cl: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 709797726-Bromo-8-chloro-3,4-dihydroquinolin-2(1H)-one

Produkt 1

HCID 722082846-Bromo-8-chloro-1-methyl-1,2,3,4-tetrahydroquinolin-2-oneAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 6-bromo-8-chloro-3,4-dihydro-1H-quinolin-2-one (7.0 g, 26.9 mmol) in DMF (100 mL) was treated with potassium tert-butoxide (6.0 g, 53.8 mmol) at 0° C. portionwise. The resulting mixture was stirred at 0° C. for 30 minutes before methyl iodide (5.0 g, 35.0 mmol) was added. After stirred for 12 hours, the reaction mixture was treated with water, extracted with EtOAc, washed with water and brine in sequence, and dried over anhydrous Na2SO4. After removal of solvent under reduced pressure, the crude product (3.3 g, 45%) was obtained as a white solid.

Aufarbeitung

  1. additionwas added
  2. extractionextracted with EtOAc
  3. washwashed with water and brine in sequence
  4. dry with materialdried over anhydrous Na2SO4
  5. customAfter removal of solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a2ef4ba7dac3402da01744e0d06b57f5
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260408B2

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