반응 #655992

반응 방정식

6-propylcarbonylamino-5-nitro-3-ethoxycarbonyl-3-methylindolin-2-one

hydrogen

→

title compound

2-Propyl-7-ethoxycarbonyl-7-methyl-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one

용매

ethanol

반응 조건

후처리

1. 1
   기타at normal pressure and ambient temperature
2. 2
   여과the catalyst is filtered off with suction
3. 3
   기타the filtrate is evaporated to dryness
4. 4
   workup.DISTILLATIONglacial acetic acid, the glacial acetic acid is distilled off
5. 5
   workup.STIRRINGThe mixture is shaken out three times with dichloromethane
6. 6
   건조the combined dichloromethane phases are dried over anhydrous sodium sulphate
7. 7
   여과filtered
8. 8
   기타the filtrate evaporated to dryness
9. 9
   기타After crystallisation of the residue from isopropanol
10. 10
    기타there is obtained 0.4 g

실험 절차

Analogously to Example 5, 1.40 g. (4.0 mmole) 6-propylcarbonylamino-5-nitro-3-ethoxycarbonyl-3-methylindolin-2-one is suspended in 140 ml. ethanol and hydrogenated in the presence of 0.1 g. 10% palladium on charcoal at normal pressure and ambient temperature. After 270 ml. of hydrogen have been taken up, the catalyst is filtered off with suction and the filtrate is evaporated to dryness. The residue is stirred for 1 hour at 60° C. in 10 ml. glacial acetic acid, the glacial acetic acid is distilled off and the residue is taken up in water and neutralised with 2N aqueous sodium hydroxide solution. The mixture is shaken out three times with dichloromethane and the combined dichloromethane phases are dried over anhydrous sodium sulphate, filtered and the filtrate evaporated to dryness. After crystallisation of the residue from isopropanol, there is obtained 0.4 g. (33% of theory) of the title compound; m.p. 258°-261° C.

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