Stannous Chloride → 6-Amino-5,7-dichloro-1,4-dihydro-2,3-quinoxalinedione

HRID 439475

반응식

HRID 439475 반응식
[N+:1]([C:4]1[C:5]([Cl:17])=[C:6]2[C:11](=[CH:12][C:13]=1[Cl:14])[NH:10][C:9](=[O:15])[C:8](=[O:16])[NH:7]2)([O-])=O.Cl[Sn]Cl>C(O)C>[NH2:1][C:4]1[C:5]([Cl:17])=[C:6]2[C:11](=[CH:12][C:13]=1[Cl:14])[NH:10][C:9](=[O:15])[C:8](=[O:16])[NH:7]2

참가 물질

4

반응물 2

HCID 24479Stannous ChlorideHCID 199585776-Nitro-5,7-dichloro-1,4-dihydro-2,3-quinoxalinedione

생성물 1

HCID 211899536-Amino-5,7-dichloro-1,4-dihydro-2,3-quinoxalinedione수율 44.1%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

To a stirred mixture of 6-nitro-5,7-dichloro-1,4-dihydro-2,3-quinoxalinedione (81 mg, 0.295 mMol) in ethanol (3 mL) was added SnCl2 ·2H2O (331 mg, 1.47 mMol) in one portion. The mixture was refluxed at 80° C. (oil bath 90° C.) with stirring to 0.5 h, to form a clear solution and continually refluxed for another 0.5 h. It was then cooled to room temperature and the yellow precipitate was collected by filtration, followed by washing with cold ethanol (2×1 mL) to give 70 mg (97%) of crude title compound (contains minor impurities by NMR). Crystallization from DMSO/H2O gave 32 mg of pure title compound as bright yellow needles; mp: 342°-5° C. (dec. from 335° C.), changed color from 325° C. IR (KBr, cm-1): 3468, 3362, 3193, 1693, 1631, 1493, 1375; NMR (1H, DMSO-d6): δ5.418 (s, 2H); 6.999 (s, 1H); 11.238 (s, 1H); 11.776 (s, 1H). HRMS: calcd for C8H5N3O2Cl2 (M+) m/z: 244.9757; found 244.9769. Potency relative to DCK: 8.6%.

후처리

  1. customto form a clear solution
  2. temperaturecontinually refluxed for another 0.5 h
  3. temperatureIt was then cooled to room temperature
  4. filtrationthe yellow precipitate was collected by filtration
  5. washby washing with cold ethanol (2×1 mL)
  6. customto give 70 mg (97%) of crude title compound (contains minor impurities by NMR)
  7. customCrystallization from DMSO/H2O

출처 및 근거

ORD 기록
ord-6aecb951538f481189a738b8dc56247d
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05514680

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