Reaktion #353794

Reaktionsgleichung

acetic acid

9-nitro-N-(1-hexylheptyl)perylene-3,4-dicarboximide

water

KOH

→

9-Acetamido-N-(1-hexylheptyl)perylene-3,4-dicarboximide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe red suspension is refluxed for 4.5 h, during which a slow colour change from red to red-brown and purple and then to dark-purple
2. 2
   ExtraktionThe suspension which is now reddish purple is extracted three times with chloroform
3. 3
   Trocknenthe combined organic phases are dried with anhydrous sodium sulfate
4. 4
   Sonstigethen evaporated on a rotary evaporator
5. 5
   Sonstigethe purple-coloured product obtained
6. 6
   FiltrationThis product is filtered by chromatography on silica gel
7. 7
   Sonstigeleaving the silica gel
8. 8
   ExtraktionThe red-coloured silica gel is extracted with chloroform
9. 9
   Sonstigeto give
10. 10
    Sonstigeafter evaporation
11. 11
    Sonstigeon a rotary evaporator, 50 mg of a red powder which
12. 12
    Sonstigeis then recrystallized by extraction with methanol
13. 13
    Sonstigefrom 172°-175° C.

Vorschrift

100 mg (0.18 mmol) of 9-nitro-N-(1-hexylheptyl)perylene-3,4-dicarboximide (10) are suspended in 15 ml of glacial acetic acid, 80 mg (0.72 mmol) of iron dust are then added, and the red suspension is refluxed for 4.5 h, during which a slow colour change from red to red-brown and purple and then to dark-purple can be observed. First water is added to the cooled, violet solution, and the reaction mixture is then neutralized with 10 per cent KOH. The suspension which is now reddish purple is extracted three times with chloroform, the combined organic phases are dried with anhydrous sodium sulfate then evaporated on a rotary evaporator. According to the thin-layer chromatogram (chloroform/silica gel), the purple-coloured product obtained consists of 2 main products having Rf values of 0.02 and 0.43. This product is filtered by chromatography on silica gel using chloroform until the solution leaving the silica gel is no longer violet. The red-coloured silica gel is extracted with chloroform to give, after evaporation on a rotary evaporator, 50 mg of a red powder which is then recrystallized by extraction with methanol. Yield: 30 mg (30%) of 9-acetamido-N-(1-hexylheptyl)perylene-3,4-dicarboximide, m.p. >230° C.; from 172°-175° C. onwards product turns brown. Rf (CHCl3 /glacial acetic acid 20:1; silica gel)=0.90. UV (CHCl3): λmax (ε)=506 nm (31589, broad), 356 (2995). Fluorescence (CHCl3): λmax =574 nm (broad).

Quelle