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

HRID 54343ノート

反応式

HRID 54343 の反応式
[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.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

参加物

4

反応物 2

HCID 61436Stannous chloride dihydrateHCID 199585776-Nitro-5,7-dichloro-1,4-dihydro-2,3-quinoxalinedione

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-b5c63af961c5446f91566fe19904477f
出典データセット
uspto-grants-1997_04
特許番号
US05622952

反応ノート

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