Potassium Hydroxide → 6-Nitro-7-(3-nitro-4-oxo-4H-pyridin-1-yl-)-1,4-dihydroquinoxaline-2,3-dione

HRID 1488969Notes

Reaction equation

HRID 1488969 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[OH:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25].[OH-].[K+]>CS(C)=O>[N+:14]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:21]1[CH:22]=[CH:23][C:18](=[O:17])[C:19]([N+:24]([O-:26])=[O:25])=[CH:20]1)[NH:9][C:8](=[O:12])[C:7](=[O:13])[NH:6]2)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 99912306-Fluoro-7-nitro-1,4-dihydroquinoxaline-2,3-dioneHCID 178526806HCID 178526806, compound

Product 1

HCID 229035696-Nitro-7-(3-nitro-4-oxo-4H-pyridin-1-yl-)-1,4-dihydroquinoxaline-2,3-dioneYield 64.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

First, 677 mg of 7-fluoro-6-nitro-1,4-dihydroquinoxaline-2,3-dione, 840 mg of 4-hydroxy-3-nitropyridine, 403 mg of powdered potassium hydroxide were added to 6 ml of dry dimethylsulfoxide. The mixture was allowed to react at 130° C. for 2 hours in a nitrogen atmosphere. The subsequent processes were conducted in the same way as in Example 2. The resultant precipitate was recrystallized with dimethylformaldehyde and water, giving 672 mg of red crystals of 6-nitro-7-(3-nitro-4-oxo-4H-pyridin-1-yl)-1,4-dihydroquinoxaline-2,3-dione

Workup

  1. customto react at 130° C. for 2 hours in a nitrogen atmosphere
  2. customThe resultant precipitate was recrystallized with dimethylformaldehyde and water

Sources & evidence

ORD record
ord-ff3d3872a8f5421a94d939f717c6b0b0
Source dataset
uspto-grants-1997_10
Patent number
US05677305

Reaction notes

Loading…