Hydrazine → Perylenebutanoic acid

HRID 444617

Reaktionsgleichung

Reaktionsgleichung von HRID 444617
O=[C:2]([C:8]1[C:25]2=[C:26]3[C:15]([C:16]4[C:27]5[C:20](=[CH:21][CH:22]=[CH:23][C:24]2=5)[CH:19]=[CH:18][CH:17]=4)=[CH:14][CH:13]=[CH:12][C:11]3=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].NN.[OH-].[Na+]>C(O)COCCO>[C:8]1([CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])[C:25]2=[C:26]3[C:15]([C:16]4[C:27]5[C:20](=[CH:21][CH:22]=[CH:23][C:24]2=5)[CH:19]=[CH:18][CH:17]=4)=[CH:14][CH:13]=[CH:12][C:11]3=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 9321HydrazineHCID 14798Sodium HydroxideHCID 86645554gamma-Oxo-4-(perylen-1-yl)butanoic acid

Produkt 1

HCID 86605548Perylenebutanoic acidAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8117Diethylene GlycolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. waitfollowed by 90-minute
  2. temperaturerefluxing in a 180-° C
  3. distillationThe excess hydrazine and water were distilled away
  4. customto precipitate a solid substance
  5. filtrationThe solid substance was collected by filtration
  6. washwas washed with ion-exchange water and 2M hydrochloric acid
  7. customby drying under reduced pressure
  8. additionThis solid substance was dispersed in 10 ml of xylene
  9. temperaturewas heated to 140° C
  10. dissolutionIn this manner, the solid substance was dissolved
  11. temperatureAfter that, the substance was cooled slowly back to room temperature
  12. customto precipitate a solid substance
  13. filtrationThe solid substance generated here was collected by filtration
  14. customwas dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d38c11e224bd41f6b9c6095757efb3f8
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08475685B2

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