O-Phenylenediamine → 2,3-bis(4-aminophenyl)-quinoxaline

HRID 1796959Notes

Reaction equation

HRID 1796959 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)=O)=O)=[CH:4][CH:3]=1.[C:19]1([NH2:26])[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH2:25]>C(O)(=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=3)=[N:26][C:19]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:25]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 2751371,2-Bis(4-aminophenyl)-1,2-ethanedione

Product 1

HCID 4591452,3-bis(4-aminophenyl)-quinoxaline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1.0 g (4.17 mmole) of 4,4′-diaminobenzil and 0.45 g of o-phenylenediamine in 250 ml glacial acetic acid was heated at 50° C. for 15 mins., then stirred for 16 hours at room temperature. The mixture was then heated to 80° C. and allowed to cool slowly. The solvent was removed under vacuum and the residue was redissolved in ethanol and that was removed under vacuum.

Workup

  1. temperatureThe mixture was then heated to 80° C.
  2. temperatureto cool slowly
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue was redissolved in ethanol
  5. customthat was removed under vacuum

Sources & evidence

ORD record
ord-ae4cc4d8f82c4b0a8705dcec0abc13ab
Source dataset
uspto-grants-2006_04
Patent number
US07034026B2

Reaction notes

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