hydroxylamine-O-sulfonic acid → 1-Amino-5,7-dichloro-1,4-dihydro-2,3-quinoxalinedione

HRID 53747

반응식

HRID 53747 반응식
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[NH:4][C:5](=[O:14])[C:6](=[O:13])[NH:7]2.[NH2:15]OS(O)(=O)=O>[OH-].[K+].O>[NH2:15][N:7]1[C:8]2[C:3](=[C:2]([Cl:1])[CH:11]=[C:10]([Cl:12])[CH:9]=2)[NH:4][C:5](=[O:14])[C:6]1=[O:13]

참가 물질

5

반응물 2

HCID 76284hydroxylamine-O-sulfonic acidHCID 6502605,7-Dichloro-1,4-dihydroquinoxaline-2,3-dione

생성물 1

HCID 199586181-Amino-5,7-dichloro-1,4-dihydro-2,3-quinoxalinedione수율 69%

시약·촉매·용매 2

HCID 962Water용매HCID 14797Potassium Hydroxide용매

반응 조건

온도
60 °C

실험 절차

The procedure of Wallace, R. G., Org. Prep. Proc. Int. 14: 269 (1982) was adapted. 5,7-Dichloro-1,4-dihydroquinoxaline-2,3-dione (52 mg, 0.225 mmole) was dissolved in 3N KOH (1 mL) at 60° C. for 0.5 h, and NH2OSO3H (30 mg, 0.265 mmole, Aldrich) in distilled water (0.5 mL) was dropwise added into above solution with stirring at 60° C. Some precipitate came out after 15 mins. The mixture was stirred at room temperature overnight. The white precipitate was collected by filtration, washed with cold distilled water (0.5 mL) and dried on rotavapor at 60° C. for 2 h affording crude 1-amino-5,7-dichloro-1,4-dihydro-2,3-quinoxalinedione (38 mg, 69%), which included a little of the isomer (4-amino-5,7-dichloro-2,3-quinoxalinedione) by 1H NMR (it is not known which isomer is present in a greater amount).

후처리

  1. stirringThe mixture was stirred at room temperature overnight
  2. filtrationThe white precipitate was collected by filtration
  3. washwashed
  4. distillationwith cold distilled water (0.5 mL)
  5. customdried on rotavapor at 60° C. for 2 h

출처 및 근거

ORD 기록
ord-4c5d952d5e704bfdac91a8ae748464b9
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620979

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