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

HRID 439476Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[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[CH:5]=[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

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred mixture of 6-nitro-7-chloro-1,4-dihydro-2,3-quinoxalinedione (35 mg, 0.145 mMol) in ethanol (2 mL) was added SnCl2 ·2H2O (163 mg, 0.724 mMol) in one portion. The mixture was refluxed at 80° C. (oil bath 90° C.) with stirring for 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 (1×1 mL) to give 25 mg (82%) of crude title compound (contains minor impurities by NMR). Crystallization from DMSO/H2O gave 14 mg of pure title compound as bright yellow needles, mp:>350° C. (dec. from 335° C.). IR (KBr, cm-1): 3406, 3356, 3212, 1668, 1637, 1518, 1437. NMR (1H, DMSO-d6): d 5.306 (s, 2H); 6.551 (s, 1H); 6.940 (s, 1H); 11.606 (s, 1H); 11.788 (s, 1H). HRMS: calcd for C8H6N3O2Cl (M+) m/z: 211.0147; found 211.0159. Potency relative to DCK: 28.0%.

Workup

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 (1×1 mL)
customto give 25 mg (82%) of crude title compound (contains minor impurities by NMR)
customCrystallization from DMSO/H2O

Sources & evidence

ORD record: ord-6a6e71ff48cf41869abd53090333aa30
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05514680

Reaction notes

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