Stannous chloride dihydrate → 5-Amino-6,7-dibromo-1,4-dihydro-2,3-quinoxalinedione

HRID 53755노트

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HRID 53755 반응식
[N+:1]([C:4]1[C:13]([Br:14])=[C:12]([Br:15])[CH:11]=[C:10]2[C:5]=1[NH:6][C:7](=[O:17])[C:8](=[O:16])[NH:9]2)([O-])=O.O.O.Cl[Sn]Cl>C(O)C>[NH2:1][C:4]1[C:13]([Br:14])=[C:12]([Br:15])[CH:11]=[C:10]2[C:5]=1[NH:6][C:7](=[O:17])[C:8](=[O:16])[NH:9]2

참가 물질

4

반응물 2

HCID 61436Stannous chloride dihydrateHCID 9799201Acea-1031

생성물 1

HCID 105207625-Amino-6,7-dibromo-1,4-dihydro-2,3-quinoxalinedione수율 64.7%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

To a stirred mixture of 5-nitro-6,7-dibromo-1,4-dihydro-2,3-quinoxalinedione (327 mg, 0.89 mMol) in ethanol (10 mL) was added SnCl2.2H2O (1.0 g, 4.45 mMol) in one portion. The mixture was refluxed at 80° C. (oil bath 90° C.) with stirring for 4 h. The mixture was then cooled to room temperature and the yellow precipitate was collected by filtration, followed by washing with cold ethanol (2×1 mL), to get 227 mg (76%) of crude title product (contains minor impurities by NMR). Crystallization from DMSO/H2O gave 193 mg of pure title product as bright yellow needles; mp: 324°-6° C. (dec.), changed color from 270° C. IR (KBr, cm-1): 3456; 3281; 1700; 1643. NMR (1H, DMSO-d6): d 5.844 (s, 2H); 6.732 (s, 1H); 11.257 (s, 1H); 11.810 (s, 1H). Purity: >96.96% by HPLC. HRMS: calcd for C8H8N3O2Br2 (M+) m/z 332.8747; found: 332.8754. Potency relative to DCK: 341%.

후처리

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationthe yellow precipitate was collected by filtration
  3. washby washing with cold ethanol (2×1 mL)
  4. customto get 227 mg (76%) of crude title product (contains minor impurities by NMR)
  5. customCrystallization from DMSO/H2O

출처 및 근거

ORD 기록
ord-e1f0b05b9793435c962120d844916185
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620979

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