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

HRID 54380Notes

Reaction equation

HRID 54380 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[Cl:14])[NH:10][C:9](=[O:15])[C:8](=[O:16])[NH:7]2)([O-:3])=[O:2].[N+:17]([O-])([O-:19])=[O:18].[K+]>OS(O)(=O)=O>[N+:17]([C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[C:13]([Cl:14])[CH:12]=[C:11]2[C:6]=1[NH:7][C:8](=[O:16])[C:9](=[O:15])[NH:10]2)([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 106101506-Chloro-7-nitro-quinoxaline-2,3-diol

Product 1

HCID 104934845,6-Dinitro-7-chloro-1,4-dihydro-2,3-quinoxalinedioneYield 70.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
4 °C

Procedure

To a solution of 6-nitro-7-chloro-1,4-dihydro-2,3-quinoxalinedione (120 mg, 0.50 mmol) in concentrated H2SO4 (1.0 mL) was added KNO3 (61 mg, 0.60 mmol, Baker). The mixture was stirred at 4° C. for 2 days, then ice (2 g) was added. The precipitate was collected by filtration and the solid was dissolved in 1N NaOH (5 mL) and filtered. The filtrate was acidified to pH=2 with 4N HCl (~1.2 mL) to give a yellow precipitate, which was collected by filtration and was washed with water (2×1 mL), then was dried at 50° C. for 4 h, affording crude title compound (101 mg, 70%) as a yellow 1.5 powder. The crude compound (100 mg) was dissolved into acetone (2 mL) and the insoluble material was removed by centrifugation. Water (1 mL) was added to the clear solution of acetone and the resultant solution was allowed to stand at 4° C. overnight to give purer compound. Recrystallization from acetone/water again gave pure title compound (55 mg). Mp: 298°-300° C. (dec.); IR (KBr, cm-1): 3434, 3295, 3111, 2920, 1716, 1571. 1H NMR (DMSO-d6): δ12.560 (s, 1H), 12.421 (s, 1H), 7.442 (s, 1H). HRMS; calcd for C8H3ClN4O6 (M+) m/z: 285.9740, found: 285.9741.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. dissolutionthe solid was dissolved in 1N NaOH (5 mL)
  3. filtrationfiltered
  4. customto give a yellow precipitate, which
  5. filtrationwas collected by filtration
  6. washwas washed with water (2×1 mL)
  7. customwas dried at 50° C. for 4 h

Sources & evidence

ORD record
ord-daa573d2af85415db7c50b026461e97a
Source dataset
uspto-grants-1997_04
Patent number
US05622952

Reaction notes

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