Nitric Acid → 6-Bromo-7-chloro-5-nitroquinoxaline-2(1H)-one

HRID 1068608Notes

Reaction equation

HRID 1068608 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[CH2:6][NH:5]2.[N+:14]([O-])([OH:16])=[O:15]>C(O)(C(F)(F)F)=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])[CH:6]=[N:5]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 100383166-bromo-7-chloro-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 211899856-Bromo-7-chloro-5-nitroquinoxaline-2(1H)-oneYield 70%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred suspension of 6-bromo-7-chloro-3,4-dihydroquinoxaline-2(1H)-one (0.06 g, 0.23 mmol, as obtained above) in CF3COOH (0.5 mL) was added fuming HNO3 (0.02 mL, 0.46 mmol) and the resulting reddish yellow suspension was stirred at room temperature overnight The cream colored suspension so obtained was poured into ice (2.5 mL) and the precipitated solid was filtered, washed with water (1.0 mL), and dried under vacuum to afford 0.049 g (70%) of the title compound as a cream colored powder. 1H NMR (DMSO-d6): δ 7.577 (s, 1H), 8.251 (s, 1H), 12.879 (s, 1H). The crude product was used as such for the final reaction.

Workup

  1. customso obtained
  2. filtrationthe precipitated solid was filtered
  3. washwashed with water (1.0 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-98544b832cc34fe1b3820743489efef5
Source dataset
uspto-grants-2001_06
Patent number
US06251903B1

Reaction notes

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