Ethylenediamine → 6,11-Dibromodibenzo[f,h]quinoxaline

HRID 1751382Notes

Reaction equation

HRID 1751382 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([Br:16])=[CH:10][CH:11]=3)[C:6](=O)[C:5](=O)[C:4]=2[CH:3]=1.[CH2:19]([NH2:22])[CH2:20][NH2:21]>C(O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4]([CH:3]=1)=[C:5]1[C:6](=[C:7]3[CH:8]=[C:9]([Br:16])[CH:10]=[CH:11][C:12]=23)[N:22]=[CH:19][CH:20]=[N:21]1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 2658432,7-dibromophenanthrene-9,10-dione

Product 1

HCID 591885516,11-Dibromodibenzo[f,h]quinoxalineYield 34.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2,7-dibromophenanthrene-9,10-dione (1.0 g, 2.7 mmol), ethylenediamine (1.8 mL, 26.9 mmol) and ethanol (20 mL) was heated to 85° C. After 3 hours, the reaction was cooled to room temperature and the solids were filtered and thoroughly washed methanol to yield 6,11-dibromodibenzo[f,h]quinoxaline (360 mg, 34%).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. filtrationthe solids were filtered

Sources & evidence

ORD record
ord-28f8234463ce4f9585f15bc9a32bb97b
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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