Methyl iodide → 5,6,7,8-tetrahydro-5-oxo-1,7,7-trimethyl-2(1H)-quinolinone

HRID 1587001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1587001
[CH3:1][C:2]1([CH3:14])[CH2:11][C:10]2[NH:9][C:8](=[O:12])[CH:7]=[CH:6][C:5]=2[C:4](=[O:13])[CH2:3]1.CI.[C:17](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:13]=[C:4]1[CH2:3][C:2]([CH3:14])([CH3:1])[CH2:11][C:10]2[N:9]([CH3:17])[C:8](=[O:12])[CH:7]=[CH:6][C:5]1=2

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135163797,7-dimethyl-7,8-dihydroquinoline-2,5(1H,6H)-dione

Produkt 1

HCID 190261755,6,7,8-tetrahydro-5-oxo-1,7,7-trimethyl-2(1H)-quinolinoneAusbeute 50,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-2(1H)-quinolinone (15.0 g), methyl iodide (12.3 g), potassium carbonate (21.6 g), and dimethylformamide (230 ml) was stirred at room temperature for 21 hrs. The reaction mixture was filtered, and the filtrate was concentrated. Ethyl acetate was added to the residue, and the mixture was filtered. The filtrate was washed with brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated to give 8.1 g (50%) of 5,6,7,8-tetrahydro-5-oxo-1,7,7-trimethyl-2(1H)-quinolinone.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. additionEthyl acetate was added to the residue
  4. filtrationthe mixture was filtered
  5. washThe filtrate was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-7c81b9949c8a4536b20e31229ed47a77
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05216164

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