O-Phenylenediamine → 2-(4-Hydroxy-3-methoxy-5-nitrophenyl)quinoxaline

HRID 725330Notes

Reaction equation

HRID 725330 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([OH:14])=[C:7]([O:15][CH3:16])[CH:6]=1)=O.[C:17]1([NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH2:23].C([O-])(=O)C.[Na+]>CO>[OH:14][C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]([C:3]2[CH:2]=[N:24][C:17]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:23]=2)=[CH:6][C:7]=1[O:15][CH3:16]

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 517045Sodium AcetateHCID 144509832-Bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone

Product 1

HCID 1356653242-(4-Hydroxy-3-methoxy-5-nitrophenyl)quinoxaline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

ada) A suspension of 14.5 g of 2-bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone and 5.41 g of 1,2-phenylenediamine in 350 ml of methanol is treated with 4.92 g of sodium acetate and the mixture is heated to boiling under reflux for 22 hours. The reaction mixture is then evaporated, the residue is dissolved in methylene chloride, this solution is washed four times with water, dried over sodium sulfate, filtered and evaporated. There is obtained 2-(4-hydroxy-3-methoxy-5-nitrophenyl)quinoxaline of m.p. 195°-197° (from methylene chloride/methanol).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 22 hours
  3. customThe reaction mixture is then evaporated
  4. dissolutionthe residue is dissolved in methylene chloride
  5. washthis solution is washed four times with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4fcd1fe329a1452da72ec9b68e3c6510
Source dataset
uspto-grants-1998_01
Patent number
US05705703

Reaction notes

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