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

HRID 439475

Reaktionsgleichung

[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

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

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%.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-6aecb951538f481189a738b8dc56247d
Quelldatensatz: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05514680

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