Methyl iodide → 8-methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 503985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503985
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9][CH2:8]2.[H-].[Na+].[H][H].[CH3:18]I>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]([CH3:18])[C:10](=[O:13])[CH2:9][CH2:8]2

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 133754763,4-Dihydro-8-methoxy-2(1H)-quinolinoneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 133841968-methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-oneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

8-Methoxy-3,4-dihydro-1H-quinolin-2-one (15 g) was dissolved in DMF (150 ml), and 3.6 g of sodium hydride (60% in oil) was added under ice cooling. After the addition, stirring was carried out at room temperature until the generation of hydrogen stopped. The resulting mixture was cooled with ice water again, and 5.8 ml of methyl iodide was added dropwise, followed by stirring at room temperature overnight. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to thereby obtain 16.7 g (yield: 96%) of 8-methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one.

Aufarbeitung

  1. additionAfter the addition
  2. stirringby stirring at room temperature overnight
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0ff5eaa87a1d47c9bb68144dbd36f2b9
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07777038B2

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