Water → 6-Bromo-7-chloro-1-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 1774834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1774834
[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[Cl:18])[NH:14][C:13](=[O:19])[CH2:12][CH2:11]2.CI.O>CN(C=O)C>[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[Cl:18])[N:14]([CH3:1])[C:13](=[O:19])[CH2:12][CH2:11]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 709793626-Bromo-7-chloro-3,4-dihydroquinolin-2(1H)-one

Produkt 1

HCID 866791856-Bromo-7-chloro-1-methyl-3,4-dihydro-1H-quinolin-2-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Potassium tert-butoxide (0.45 g, 4.0 mmol) was added to a solution of 6-bromo-7-chloro-3,4-dihydro-1H-quinolin-2-one (0.52 g, 2.0 mmol) in DMF (5 mL) at 0° C. Then, the reaction mixture was stirred at 0° C. for 30 min and methyl iodide (0.18 g, 1.29 mmol) was added. The resulting mixture was stirred for 2 hours before water was added. After extraction of the reaction mixture with EtOAc, the organic layer was washed with water and brine in sequence. Then, it was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to give a crude product (0.49 g, 90%) as a white solid. MS: 274.0 (M+H+)+.

Aufarbeitung

  1. additionwas added
  2. extractionAfter extraction of the reaction mixture with EtOAc
  3. washthe organic layer was washed with water and brine in sequence
  4. dry with materialThen, it was dried over anhydrous Na2SO4
  5. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3be3bf3437ab4d629f6cf74ce3801838
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260408B2

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