Réaction #531799

Équation de réaction

compound 72

γ-oxo-4-(perylen-1-yl)butanoic acid

hydrazine

sodium hydroxide

→

black solid

Rendement 99.8%

4-(perylen-1-yl)butanoic acid

Rendement 99.8%

Solvants

diethylene glycol

Conditions de réaction

Traitement

1. 1
   workup.WAITfollowed by 90-minute
2. 2
   Températurerefluxing in a 180-° C
3. 3
   workup.DISTILLATIONThe excess hydrazine and water were distilled away
4. 4
   Autreto precipitate a solid substance
5. 5
   FiltrationThe solid substance was collected by filtration
6. 6
   Lavagewas washed with ion-exchange water and 2M hydrochloric acid
7. 7
   Autreby drying under reduced pressure
8. 8
   workup.ADDITIONThis solid substance was dispersed in 10 ml of xylene
9. 9
   Températurewas heated to 140° C
10. 10
    workup.DISSOLUTIONIn this manner, the solid substance was dissolved
11. 11
    TempératureAfter that, the substance was cooled slowly back to room temperature
12. 12
    Autreto precipitate a solid substance
13. 13
    FiltrationThe solid substance generated here was collected by filtration
14. 14
    Autrewas dried under reduced pressure

Mode opératoire

The compound 72 (0.390 g, 1.11 mmol), 0.4 ml of 79% aqueous hydrazine, and 0.290 g (7.25 mmol) of sodium hydroxide were dissolved in 3.0 ml of diethylene glycol, followed by 90-minute refluxing in a 180-° C. oil bath. The excess hydrazine and water were distilled away, and the refluxing was continued for two more hours. After the reaction was completed, the solution was cooled back to room temperature, to precipitate a solid substance. The solid substance was collected by filtration, and was washed with ion-exchange water and 2M hydrochloric acid, followed by drying under reduced pressure. This solid substance was dispersed in 10 ml of xylene, and was heated to 140° C. In this manner, the solid substance was dissolved. After that, the substance was cooled slowly back to room temperature, to precipitate a solid substance. The solid substance generated here was collected by filtration, and was dried under reduced pressure, to obtain 0.375 g of the black solid substance 73.

Source