Acenaphthenequinone → 9-(Trifluoromethyl)acenaphtho[1,2-b]quinoxaline

HRID 461667

Reaktionsgleichung

Reaktionsgleichung von HRID 461667
[C:1]1(=O)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[C:2]1=O.[NH2:15][C:16]1[C:21]([N+]([O-])=O)=[CH:20][C:19]([C:25]([F:28])([F:27])[F:26])=[CH:18][C:17]=1[N+:29]([O-])=O.[H][H]>[Pd].C(O)C>[F:26][C:25]([F:27])([F:28])[C:19]1[CH:18]=[C:17]2[C:16](=[CH:21][CH:20]=1)[N:15]=[C:2]1[C:3]3[CH:4]=[CH:5][CH:6]=[C:7]4[C:12]=3[C:11]([C:1]1=[N:29]2)=[CH:10][CH:9]=[CH:8]4

Komponenten

6

Edukt 3

HCID 6724AcenaphthenequinoneHCID 99362,6-Dinitro-4-(trifluoromethyl)aniline2×HCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 126241029-(Trifluoromethyl)acenaphtho[1,2-b]quinoxalineAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Acenaphthenequinone, 9.1 g. (0.05m), and 10.3 g. (0.05m) of 4-amino-3-nitrobenzotrifluoride were hydrogenated at room temperature in 125 ml. of 2B ethanol with 2.5 g. of palladium-on-carbon (5 percent) at 50 psi. After 4 hours three equivalents of hydrogen were absorbed and the temperature rose to 40° C. The catalyst was filtered and the filtrate was diluted with 1.2 l. of ethanol. The reaction was completed by refluxing the ethanolic solution for about 1 hour. The precipitated product was collected to yield about 8 g. (50 percent yield) of 9-(trifluoromethyl)acenaphtho[1,2-b]quinoxaline, mp = 185°-186° C.

Aufarbeitung

  1. customwere hydrogenated at room temperature in 125 ml
  2. customrose to 40° C
  3. filtrationThe catalyst was filtered
  4. additionthe filtrate was diluted with 1.2 l
  5. temperatureby refluxing the ethanolic solution for about 1 hour
  6. customThe precipitated product was collected
  7. customto yield about 8 g

Quellen und Nachweise

ORD-Eintrag
ord-0ad9a4b1ec14493b94feb95eda397d2f
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04064127

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