O-Phenylenediamine → 2-(4-Bromophenyl)-3-phenylquinoxaline

HRID 2408217Notes

Reaction equation

HRID 2408217 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1.[C:18]1([NH2:25])[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH2:24]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:25][C:18]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:24]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 2367011-(4-Bromophenyl)-2-phenylethane-1,2-dione

Product 1

HCID 18497902-(4-Bromophenyl)-3-phenylquinoxaline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 200-mL flask were placed 4.5 g (15 mmol) of 1-(4-bromophenyl)-2-phenylethanedione, 1.8 g (17 mmol) of 1,2-phenylenediamine, and 50 mL of ethanol. This solution was refluxed under a nitrogen stream for 2.5 hours. After a predetermined time, the solution was cooled to room temperature, and the precipitated solid was collected by suction filtration. The collected solid was washed with ethanol; thus, 5.2 g of a white powder which was a product was obtained in a yield of 92%.

Workup

  1. customIn a 200-mL flask were placed
  2. temperatureThis solution was refluxed under a nitrogen stream for 2.5 hours
  3. filtrationthe precipitated solid was collected by suction filtration
  4. washThe collected solid was washed with ethanol
  5. customwas obtained in a yield of 92%

Sources & evidence

ORD record
ord-83a293a63c584bc799bc68a49bc9bb00
Source dataset
uspto-grants-2014_08
Patent number
US08815412B2

Reaction notes

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