9,10-Phenanthrenedione → 2-(3-Bromophenyl)dibenzo[f,h]quinoxaline

HRID 1751329Notes

Reaction equation

HRID 1751329 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH2:11])[CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].[CH:14]1[C:27]2[C:26](=O)[C:25](=O)[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]=2[CH:17]=[CH:16][CH:15]=1>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[N:10][C:26]3[C:25](=[C:24]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]4=[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:27]4=3)[N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 67639,10-PhenanthrenedioneHCID 14797Potassium HydroxideHCID 227566651-(3-Bromophenyl)ethane-1,2-diamine

Product 1

HCID 867038242-(3-Bromophenyl)dibenzo[f,h]quinoxalineYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First, in a 500 mL three-neck flask were put 2.5 g of 1-(3-bromophenyl)ethane-1,2-diamine, 0.62 g of potassium hydroxide, and 200 mL of dry ethanol, and the air in the flask was replaced with nitrogen. The solution in the flask was refluxed for 2 hours, 2.1 g of 9,10-phenanthrenequinone was added thereto, and the solution was refluxed for 9 hours. After that, the obtained mixture was suction-filtered, and the resulting solid was washed with ethanol to give 2-(3-bromophenyl)dibenzo[f,h]quinoxaline as a yellow-white solid in a yield of 70%.

Workup

  1. customFirst, in a 500 mL three-neck flask were put
  2. temperatureThe solution in the flask was refluxed for 2 hours
  3. temperaturethe solution was refluxed for 9 hours
  4. filtrationAfter that, the obtained mixture was suction-filtered
  5. washthe resulting solid was washed with ethanol

Sources & evidence

ORD record
ord-f3b1917870684f14aa6935c55b491f99
Source dataset
uspto-grants-2015_10
Patent number
US09159934B2

Reaction notes

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