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

HRID 2398060

Reaction equation

HRID 2398060 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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 one 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.

Workup

  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 of ethanol
  5. temperatureby refluxing the ethanolic solution for about one hour
  6. customThe precipitated product was collected
  7. customto yield about 8 g

Sources & evidence

ORD record
ord-7d9460a757b544e6a7880fa2a3827817
Source dataset
uspto-grants-1977_05
Patent number
US04024142

Linked notes

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