O-Phenylenediamine → 2-(3-nitrophenyl)quinoxaline

HRID 2045909Notes

Reaction equation

HRID 2045909 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=O.[C:14]1([NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:20].C([O-])(=O)C.[Na+]>C(O)C>[N+:11]([C:7]1[CH:6]=[C:5]([C:3]2[CH:2]=[N:21][C:14]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:20]=2)[CH:10]=[CH:9][CH:8]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 517045Sodium Acetate

Product 1

HCID 7377362-(3-nitrophenyl)quinoxalineYield 59.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(3-nitrophenyl)ethanone (20.5 g, 84 mmol), 1,2-phenylenediamine (8.6 g, 80 mmol) and sodium acetate (12.2 g, 90 mmol) in ethanol (EtOH) (250 mL) was heated at reflux for 5 hrs. The reaction mixture was cooled to room temperature, filtered, washed with EtOH and water, and dried to afford 2-(3-nitrophenyl)quinoxaline (11.9 g, 59% yield). LCMS calculated for C14H9N3O2 (M+H): 252.25. found 252; (M+H+MeCN): 293.10. found 293. 1H-NMR (400 MHz, DMSO-d6) δH: 9.62 (1H, s), 9.12 (1H, m), 8.81 (1H, m), 7.42 (1H, m), 8.30-8.10 (2H, m), 8.00-7.82 (3H, m).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hrs
  3. filtrationfiltered
  4. washwashed with EtOH and water
  5. customdried

Sources & evidence

ORD record
ord-07c48719bfd74eba99bcf034987be19d
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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