Reaktion #90096

Reaktionsgleichung

4-(6,6-dimethyl-2-nitro-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-8-yl oxy)-piperidine-1-carboxylic acid tert-butyl ester

ammonium chloride

→

title compound

Ausbeute 118.5%

4-(2-Amino-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-8-yl oxy)-piperidine-1-carboxylic acid tert-butyl ester

Ausbeute 118.5%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONdistilled water (4 ml)
2. 2
   workup.ADDITIONwere added
3. 3
   SonstigeUpon the completion of the reaction, insoluble matters
4. 4
   Filtrationwere filtered off
5. 5
   Extraktionthe filtrate was extracted with ethyl acetate
6. 6
   WaschenThe organic layer was washed with brine
7. 7
   Trocknendried over sodium sulfate
8. 8
   SonstigeThe drying agent was removed by filtration
9. 9
   Sonstigethe residues obtained
10. 10
    Einengenafter concentration under reduced pressure
11. 11
    Sonstigewere purified by silica gel column chromatography (ethyl acetate/hexane)

Vorschrift

To the ethanol (8 ml) suspension of 4-(6,6-dimethyl-2-nitro-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-8-yl oxy)-piperidine-1-carboxylic acid tert-butyl ester (Compound P4, 103 mg, 0.204 mmol), iron powder (228 mg, 20 eq.), ammonium chloride (109 mg, 10 eq.), and distilled water (4 ml) were added and the mixture was stirred at 90° C. for 30 min. Upon the completion of the reaction, insoluble matters were filtered off, and the filtrate was extracted with ethyl acetate. The organic layer was washed with 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 silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (115 mg, 57%).

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