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

HRID 53816Notes

Reaction equation

HRID 53816 reaction equation
[Br:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[CH:6]=[N:5]2.[N+]([O-])([O-])=[O:18].[K+]>OS(O)(=O)=O>[Br:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[C:6](=[O:18])[NH:5]2

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 211899856-Bromo-7-chloro-5-nitroquinoxaline-2(1H)-one

Product 1

HCID 104037516-Bromo-7-chloro-5-nitro-1,4-dihydro-2,3-quinoxalinedioneYield 50%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution of 6-bromo-7-chloro-5-nitroquinoxaline-2(1H)-one (0.025 g, 0.082 mmol) in conc. H2SO4 (0.5 mL) was added KNO3 (0.011 g, 0.11 mmol) and the resulting dark red solution was stirred at r.t. for 65 h. The solution was then cooled in an ice-bath and diluted with ice to a total volume of 5.0 mL. The precipitated solid was filtered, washed with water (2.0 mL) and dried under vacuum to give 0.019 g (72%) of crude product. It was purified as follows. Crude product (0.016 g) was taken up in 1N NaOH (1.1 mL). The mixture was centrifuged and the supernatant liquid was acidified with conc. HCl to pH ~2. The precipitated solid was filtered, washed with water (1.0 mL) and dried under vacuum to furnish 0.010 g (50%) of pure title compound as a cream colored powder; m.p. 338°-343° C. (decomposed); 1H NMR (DMSO-d6): 7.351 (s, 1H), 12.251 (s overlapped by a br s, 2H).

Workup

  1. temperatureThe solution was then cooled in an ice-bath
  2. additiondiluted with ice to a total volume of 5.0 mL
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water (2.0 mL)
  5. customdried under vacuum
  6. customto give 0.019 g (72%) of crude product
  7. customIt was purified
  8. filtrationThe precipitated solid was filtered
  9. washwashed with water (1.0 mL)
  10. customdried under vacuum

Sources & evidence

ORD record
ord-09e44261d66145a187d5c24cc4d970b1
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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