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

HRID 2043807Notes

Reaction equation

HRID 2043807 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 recovery flask were placed 4.5 g (15 mmol) of 1-(4-bromophenyl)-2-phenylethanedione, 1.8 g (17 mmol) of ortho-phenylenediamine, and 50 mL of ethanol. This solution was refluxed under 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 target white powder was obtained with a yield of 92%.

Workup

  1. customIn a 200 mL recovery flask were placed
  2. temperatureThis solution was refluxed under nitrogen stream for 2.5 hours
  3. filtrationthe precipitated solid was collected by suction filtration
  4. washThe collected solid was washed with ethanol
  5. customthus, 5.2 g of target white powder was obtained with a yield of 92%

Sources & evidence

ORD record
ord-6ac2a91370bd4386b0a7133b0412e66d
Source dataset
uspto-grants-2013_11
Patent number
US08586740B2

Reaction notes

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