Potassium Nitrate → 6-Trifluoromethyl-7-nitro-1,4-dihydro-2,3-quinoxalinedione

HRID 439451Notes

Reaction equation

[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7](=[O:14])[NH:6]2.[N+:17]([O-])([O-:19])=[O:18].[K+]>OS(O)(=O)=O>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:17]([O-:19])=[O:18])[NH:9][C:8](=[O:13])[C:7](=[O:14])[NH:6]2

Participants

Conditions

Temperature: 0 °C

Procedure

The title compound was prepared using an adaptation of the method of Cheeseman (Cheeseman, G. W. H., J. Chem. Soc. 1171 (1962)). 6-Trifluoromethyl-1,4-dihydro-2,3-quinoxalinedione (200 mg, 0.869 mmol) was dissolved in 8 mL of concentrated H2SO4 and the yellow-green solution was cooled to 0° C. with stirring. To this was added in small portions KNO3 (87.8 mg, 1.10 mmol). The reaction was allowed to stir 1 h at 0° C. and then was allowed to come to room temperature and stir overnight. The brown-orange reaction mixture was then poured into 10 mL ice H2O. The product was isolated by vacuum filtration as pale yellow crystals which were rinsed with a small amount of cold H2O and air dried. The crystals were further dried under vacuum (0.1 torr, 25° C.) to yield 121.1 mg (50.6% yield). 1H NMR (d6 -DMSO) δ7.53 (s, 1H, ArH), 7.80 (s, 1H, ArH), 12.4 (s, 2H, NH). EIMS m/z 275 (81, M+), 217 (36), 201 (100, bp), EIHRMS calc. for C9H4N3O4F3 275.0153, found 275.0170.

Workup

stirringto stir 1 h at 0° C.
customto come to room temperature
stirringstir overnight
customThe product was isolated by vacuum filtration as pale yellow crystals which
washwere rinsed with a small amount of cold H2O and air
customdried
customThe crystals were further dried under vacuum (0.1 torr, 25° C.)
customto yield 121.1 mg (50.6% yield)

Sources & evidence

ORD record: ord-85036c36a732490a8d9c567675838f79
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05514680

Reaction notes

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