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

HRID 719039

Reaction equation

HRID 719039 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]quinoxaline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First, into 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 atmosphere in the flask was replaced with nitrogen. A reaction container was heated, the reacted solution was refluxed for two hours, 2.1 g of 9,10-phenanthrenequinone was added thereto, and the mixture was refluxed for nine hours. Then, the obtained mixture was subjected to suction filtration, and washed with ethanol, thereby obtaining 2-(3-bromophenyl)dibenzo[f,h]quinoxaline (a yellow white solid, a collection rate of 70%).

Workup

  1. customFirst, into a 500-mL three-neck flask were put
  2. temperatureA reaction container was heated
  3. temperaturethe reacted solution was refluxed for two hours
  4. temperaturethe mixture was refluxed for nine hours
  5. filtrationThen, the obtained mixture was subjected to suction filtration
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-fb463001fe3d4ce48b21cc095b6a1da3
Source dataset
uspto-grants-2015_11
Patent number
US09196844B2

Linked notes

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