Reaktion #156239

Reaktionsgleichung

4-Chloro-3-phenyl-1H-quinoline-2-one

Sodium hydride

1-Ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

→

title compound

Ausbeute 42.8%

7-[3-(4-chloro-2-oxo-3-phenyl-2H-quinolin-1-yl)propoxy]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Ausbeute 42.8%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 7 days
2. 2
   Sonstigethe generated insoluble matter was separated
3. 3
   workup.DISSOLUTIONThe insoluble matter was dissolved in ethyl acetate
4. 4
   TrocknenThe liquid was dried over sodium sulfate and condensed under reduced pressure
5. 5
   SonstigeThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:3)
6. 6
   Sonstigecondensed under reduced pressure
7. 7
   Sonstigethe residue was recrystallized from ether

Vorschrift

4-Chloro-3-phenyl-1H-quinoline-2-one (0.3 g) was suspended in DMF (6 ml). Sodium hydride (60% in oil) (51 mg) was added, and the mixture was stirred for 15 minutes at room temperature. 1-Ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (0.55 g) was added thereto and the mixture was stirred at room temperature for 7 days. The reaction mixture was poured to ice water (50 ml), and the generated insoluble matter was separated. The insoluble matter was dissolved in ethyl acetate. The liquid was dried over sodium sulfate and condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:3). The purified product was condensed under reduced pressure, and the residue was recrystallized from ether, thereby obtaining the title compound (0.28 g) as a white powder.

Quelle