Potassium Nitrate → 6,7-Difluoro-5-nitro-1,4-dihydro-2,3-quinoxalinedione

HRID 53793

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 55 °C

Versuchsvorschrift

To a suspension of 6,7-difluoro-1,4-dihydro-2,3-quinoxalinedione (837 mg, 4.23 mmol) in trifluoracetic acid (30 mL) was added KNO3 (5 12 mg, 5.07 mmol). The mixture was stirred at 55 ° C. for 20 h at the end of this time, 256 mg (2.50 mmol) of KNO3 was added and the reaction mixture was stirred at 55° C. for 20 h, then another 256 mg (2.50 mmol) of KNO3 was added and the mixture was stirred at 55° C. for 20 h. The reaction mixture was then rotaevaporated to dryness. To the residual solid was added ice-cold water (about 15 mL), the solid was collected by vacuum filtration, washed with ice-cold water (5×5 mL), and dried at 40° C. under 1 mm Hg for 14 h, giving 700 mg (68%) of the title compound as a yellow powder. Mp 288°-90° C. (dec.). IR (KBr) 3424, 3226, 1752, 1717, 1554, 1356, 1304 cm-1. 1H NMR (DMSO-d6): 12.249 (s, 1H), 11.864 (bs, 1H), 7.330 (dd, 1H, J=10.5, 7.8 Hz). Analysis for C8H3F2N3O4, calcd: C, 39.50, H, 1.24, N, 17.29; found: C, 39.42, H, 1.26, N, 17.08.

Aufarbeitung

additionwas added
stirringthe mixture was stirred at 55° C. for 20 h
filtrationthe solid was collected by vacuum filtration
washwashed with ice-cold water (5×5 mL)
customdried at 40° C. under 1 mm Hg for 14 h

Quellen und Nachweise

ORD-Eintrag: ord-42c8fec816d04dd5869b5c0c32c7c1a1
Quelldatensatz: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05620979

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