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

HRID 1600720Notes

Reaction equation

HRID 1600720 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. customThe cream colored suspension so obtained
  2. filtrationthe precipitated solid was filtered
  3. washwashed with water (1.0 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-673349dea77445759c67ff9ce93db6bf
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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