Water → 5-Aminoquinoxaline

HRID 992050

Reaction equation

HRID 992050 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[N:6]=[CH:7][CH:8]=[N:9]2)([O-])=O.O>CC(O)=O.[Fe]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[N:6]=[CH:7][CH:8]=[N:9]2

Participants

5

Reactant 2

HCID 962WaterHCID 97512Quinoxaline, 5-nitro-

Product 1

HCID 854945-AminoquinoxalineYield 61.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a three neck 250 mL round bottom flask equipped with a reflux condenser and nitrogen inlet was added 5-nitro-quinoxaline (4 g, 22.8 mmol) dissolved in HOAc (60 mL). The mixture was heated to boiling, removed from heat, and solid Fe powder (3.83 g, 68.6 mmol) was added. Vigorous boiling was observed. The reaction mixture was heated at reflux 10 minutes and then poured into H2O (100 mL) and ice. The aqueous solution was filtered and basified to pH>10 with 1 M NaOH, and extracted in EtOAc (3×200 mL). The organic layers were combined, dried over Na2SO4, and concentrated. The resulting oil was purified by column chromatography (40% EtOAc/Hexanes) yielding 2.03 g (61%) of an orange solid: mp 87-90° C.

Workup

  1. customTo a three neck 250 mL round bottom flask equipped with a reflux condenser and nitrogen inlet
  2. temperatureThe mixture was heated
  3. customremoved
  4. temperaturefrom heat
  5. temperatureThe reaction mixture was heated
  6. temperatureat reflux 10 minutes
  7. filtrationThe aqueous solution was filtered
  8. extractionextracted in EtOAc (3×200 mL)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customThe resulting oil was purified by column chromatography (40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-6eb657048b8649b9b295b7685a571a4b
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Linked notes

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