Reaktion #89987

Reaktionsgleichung

8-Hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Compound A6

8-Hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

2-chloroethyldiethylamine

cesium carbonate

water

→

title compound

Ausbeute 33.0%

8-(2-Diethylamino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Ausbeute 33.0%

Lösungsmittel

N,N-dimethylacetamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   WaschenThe organic layer was washed with saturated brine
3. 3
   Trocknendried over sodium sulfate
4. 4
   SonstigeThe drying agent was removed by filtration
5. 5
   Sonstigethe residues obtained
6. 6
   Einengenafter concentration under reduced pressure
7. 7
   Sonstigewere purified by amino silica gel column chromatography (ethyl acetate/hexane)

Vorschrift

8-Hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A6, 25 mg, 0.083 mmol) was dissolved in N,N-dimethylacetamide (1 mL), added with 2-chloroethyldiethylamine (16 mg, 1.1 eq.) and cesium carbonate (54 mg, 2 eq.) in order and stirred at 100° C. for 4 hr. The reaction solution was poured over water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by amino silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (11 mg, 32%).

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