Acetic Acid → 2,3-Diphenyl-5-aminoquinoxaline

HRID 1715526Notes

Reaction equation

HRID 1715526 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-])=O.[C:12]1([C:18]([C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=O)=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(=O)C>CO>[C:12]1([C:18]2[C:20]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[N:1][C:2]3[C:3](=[CH:4][CH:5]=[CH:6][C:7]=3[NH2:8])[N:9]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8651BenzilHCID 43595253-Nitro-1,2-phenylenediamine

Product 1

HCID 117793842,3-Diphenyl-5-aminoquinoxaline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.53 g (10 mmol) of 2,3-diaminonitrobenzene and 2.00 g (9.6 mmol) of benzil were placed in four-necked flask, to which 30 g of a solvent of acetic acid and methanol at a mixing ratio of 1:1 was added for dissolution. Subsequently, the mixture was reacted at a reaction temperature of 70° C. for 2 hours. After the reaction, the solvent was removed and the resulting product was extracted with a silica gel column (ethyl acetate:hexane=1:1).

Workup

  1. additionwas added for dissolution
  2. customSubsequently, the mixture was reacted at a reaction temperature of 70° C. for 2 hours
  3. customAfter the reaction
  4. customthe solvent was removed
  5. extractionthe resulting product was extracted with a silica gel column (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-153ee81618bf4690976a7897a4a8f078
Source dataset
uspto-grants-2010_09
Patent number
US07799894B2

Reaction notes

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