Reacción #90096

Ecuación de reacción

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

Rendimiento 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

Rendimiento 118.5%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISTILLATIONdistilled water (4 ml)
2. 2
   workup.ADDITIONwere added
3. 3
   OtroUpon the completion of the reaction, insoluble matters
4. 4
   Filtraciónwere filtered off
5. 5
   Extracciónthe filtrate was extracted with ethyl acetate
6. 6
   LavadoThe organic layer was washed with brine
7. 7
   Secadodried over sodium sulfate
8. 8
   OtroThe drying agent was removed by filtration
9. 9
   Otrothe residues obtained
10. 10
    Concentraciónafter concentration under reduced pressure
11. 11
    Otrowere purified by silica gel column chromatography (ethyl acetate/hexane)

Procedimiento

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%).

Fuente