Water → 1-Methyl-5, 6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HRID 722946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722946
[H-].[Na+].[NH:3]1[C:13]2=[C:14]3[C:9](=[CH:10][CH:11]=[CH:12]2)[CH2:8][CH2:7][CH2:6][N:5]3[C:4]1=[O:15].[CH3:16]I.O>CN(C)C=O>[CH3:16][N:3]1[C:13]2=[C:14]3[C:9](=[CH:10][CH:11]=[CH:12]2)[CH2:8][CH2:7][CH2:6][N:5]3[C:4]1=[O:15]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 156467025,6-Dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

Produkt 1

HCID 218869111-Methyl-5, 6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (2.36 g) was added to a solution of 5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (10 g) obtained in Reference Example 131 in dimethylformamide (100 ml), the mixture was stirred at room temperature for 1 hour, methyl iodide (3.68 ml) was added, and the mixture was stirred at room temperature for 18 hours. Water (200 g) was poured into the reaction mixture, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give a pale yellow solid (9.7 g). Further recrystallization from water-ethyl acetate afforded the title compound as colorless crystals (9.0 g).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7c03680e4c6441c0a75659e649bc9e0f
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138533B2

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