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

HRID 439465Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 439465
[Br:1][C:2]1[CH:11]=[C:10]([F: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>[Br:1][C:2]1[C:11]([N+:15]([O-:17])=[O:16])=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[NH:4][C:5](=[O:14])[C:6](=[O:13])[NH:7]2

Komponenten

4

Edukt 2

HCID 24434Potassium NitrateHCID 211900395-Bromo-7-fluoro-1,4-dihydroquinoxaline-2,3-dione

Produkt 1

HCID 199586215-Bromo-6-nitro-7-fluoro-1,4-dihydro-2,3-quinoxalinedioneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The method of Cheeseman, supra. was adapted. 5-Bromo-7-fluoro-1,4-dihydroquinoxaline-2,3-dione (77 mg, 0.30 mMol) was dissolved in concentrated H2SO4 (1 mL) at 0° C. for 30 min, and KNO3 (35 mg, 0.346 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. The mixture was poured into ice water (10 g) and the precipitate was collected by filtration. The precipitate was dissolved in 1N NaOH (10 mL), then was acidified to pH=2 with 4N HCl to give cream precipitate, which was collected by filtration, and was dried in the air at 50° C. for 4 h affording pure (by NMR) 5-bromo-6-nitro-7-fluoro-1,4-dihydro-2,3-quinoxalinedione (81 mg, 90%), as a white amorphous solid; mp: 320°-25° C. (dec. from 290° C.). IR (KBr, cm-1): 3416, 3071, 2952, 1721, 1609, 1546. NMR (1H, DMSO-d6): δ7.146 (d, J=10.2 Hz, 1H), 11.432 (s, 1H), 12.340 (s, 1H). HRMS: calcd. for C8H3N3O4BrF (M+) m/z: 302.9290, found: 302.9290.

Aufarbeitung

  1. waitat room temperature for 30 h
  2. filtrationthe precipitate was collected by filtration
  3. dissolutionThe precipitate was dissolved in 1N NaOH (10 mL)
  4. customto give cream precipitate, which
  5. filtrationwas collected by filtration
  6. customwas dried in the air at 50° C. for 4 h

Quellen und Nachweise

ORD-Eintrag
ord-31abc5c0b6764253905a2480b0af7808
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05514680

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