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

HRID 54405Notes

Reaction equation

HRID 54405 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) in CF3COOH (0.5 mL) was added fuming HNO3 (0.02 mL, 0.46 mmol) and the resulting reddish yellow suspension was stirred at r.t. 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 title compound as a cream colored powder which contained ~10% impurity (1H NMR integration); 1H NMR (DMSO-d6): δ7.577 (s, 1H), 8.251 (s, 1H), 12.879 (s, 1H). The crude product was used for the next 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-c3043a523503417b9ac5f5a99be5df40
Source dataset
uspto-grants-1997_04
Patent number
US05622952

Reaction notes

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