Potassium Nitrate → 6-Nitro-5,7-dibromo-1,4-dihydro-2,3-quinoxalinedione

HRID 439463Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]([Br:12])[CH:9]=[C:8]2[C:3]=1[NH:4][C:5](=[O:14])[C:6](=[O:13])[NH:7]2.[N+:15]([O-])([O-:17])=[O:16].[K+]>OS(O)(=O)=O>[N+:15]([C:11]1[C:2]([Br:1])=[C:3]2[C:8](=[CH:9][C:10]=1[Br:12])[NH:7][C:6](=[O:13])[C:5](=[O:14])[NH:4]2)([O-:17])=[O:16]

Participants

Conditions

Temperature: 0 °C

Procedure

The method of Cheeseman, supra. was adapted. 5,7-Dibromo-1,4-dihydroquinoxaline-2,3-dione (74 mg, 0.23 mMol) was dissolved in concentrated H2SO4 (1 mL) at 0° C. for 30 mins., and then KNO3 (28 mg, 0.27 mMol, Baker) was added to this solution. The mixture was stirred at 0° C. for 3 h and then at room temperature for 30 h. It was poured into ice water (8 g) and the precipitate was collected by filtration, was dissolved into iN KOH (5 mL), and the red precipitate was removed by filtration. The solution then was acidified to pH=2 with 4N HCl to obtain a cream precipitate, which was collected by filtration, then was dried in the air at 50° C. for 4 h, affording the pure 6-nitro-5,7-dibromo-1,4-dihydro-2,3-quinoxalinedione (71 mg, 84.5%), as a yellow powder; mp: 318°-20° C. (dec.). IR (KBr, cm-1): 3468, 3131, 3062, 2931, 1712, 1593, 1537. NMR (1H, DMSO-d6): δ7.392 (s, 1H), 11.566 (s, H), 12.274 (s, 1H). HRMS: calcd. for C8H3N3O4Br2 m/z: 362.8489, found: 62.8478.

Workup

waitat room temperature for 30 h
filtrationthe precipitate was collected by filtration
dissolutionwas dissolved into iN KOH (5 mL)
customthe red precipitate was removed by filtration
customto obtain a cream precipitate, which
filtrationwas collected by filtration
customwas dried in the air at 50° C. for 4 h

Sources & evidence

ORD record: ord-eaeba4ac98b84a9abe6957902c5ba811
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05514680

Reaction notes

Loading…