Water → 5-Aminoquinoxaline

HRID 428529

반응식

HRID 428529 반응식
[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

참가 물질

5

반응물 2

HCID 962WaterHCID 97512Quinoxaline, 5-nitro-

생성물 1

HCID 854945-Aminoquinoxaline수율 61.3%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-70fbde4cef874881a0343d3cddca50e0
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313126B1

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