Potassium Nitrate → 7-Chloro-6,8-difluoro-5-nitro-1,4-dihydroquinoxaline-2,3-dione

HRID 54388Notes

Reaction equation

HRID 54388 reaction equation
[Cl:1][C:2]1[C:3]([F:15])=[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+:16]([O-])([O-:18])=[O:17].[K+]>OS(O)(=O)=O>[Cl:1][C:2]1[C:3]([F:15])=[C:4]2[C:9]([NH:8][C:7](=[O:13])[C:6](=[O:14])[NH:5]2)=[C:10]([N+:16]([O-:18])=[O:17])[C:11]=1[F:12]

Participants

4

Reactant 2

HCID 24434Potassium Nitrate2×HCID 108235056-Chloro-5,7-difluoro-1,4-dihydroquinoxaline-2,3-dione

Product 1

HCID 105166837-Chloro-6,8-difluoro-5-nitro-1,4-dihydroquinoxaline-2,3-dioneYield 65%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 120 mg (5.16 mmol) of 6-chloro-5,7-difluoro-1,4-dihydroquinoxaline-2,3-dione in 1 mL of H2SO4 (97%) kept in ice bath was added portionwise 60 mg (0.59 mmol) of KNO3. The solution was stirred at room temperature for 14 h and 60 mg of KNO3 was added and it was stirred at room temperature for 24 h. It was diluted by ice-water (4 mL) and the mixture was filtered and washed by water, and dried to leave a yellow solid (94 mg, 65%). The solid was purified by NaOH/HCl precipitate to leave 63 mg of yellow solid, mp>250° C. 1H NMR (DMSO-d6), 12.11 (mb, 1), 12.503 (s, 1).

Workup

  1. stirringit was stirred at room temperature for 24 h
  2. filtrationthe mixture was filtered
  3. washwashed by water
  4. customdried

Sources & evidence

ORD record
ord-686dba8174794e3e89116335edafc1e3
Source dataset
uspto-grants-1997_04
Patent number
US05622952

Reaction notes

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