Hydrogen Peroxide → 6-Bromo-1-ethoxycarbonylmethylquinoxaline-2,3(1H,4H)-dione

HRID 373771Notes

Reaction equation

HRID 373771 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7](=[O:18])[CH:6]=[N:5]2.[OH:19]O>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7](=[O:18])[C:6](=[O:19])[NH:5]2

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 198084496-bromo-1-ethoxycarbonylmethylquinoxalin-2(1H)-one

Product 1

HCID 198084556-Bromo-1-ethoxycarbonylmethylquinoxaline-2,3(1H,4H)-dioneYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The above ester (1.25 g; 4 mmol) was reacted with 30% H2O2 (6 ml) in glacial acetic acid (16 ml) at 55° C. for 2 h. The mixture was cooled, the precipitate filtered off and recrystallized from dilute acetic acid to afford 1.0 g (77%) of the title compound. M.p. 282°-83° C. 1H-NMR (DMSO-d6):δ1.22 (t, 3H), 4.17 (q, 2H), 4.92 (s, 1H), 7.33 (m, 3H), 12.24 (br.s, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe precipitate filtered off
  3. customrecrystallized from dilute acetic acid

Sources & evidence

ORD record
ord-6e6f85e1e5d845e2a0ddb6cf8dcf81b7
Source dataset
uspto-grants-1992_11
Patent number
US05166155

Reaction notes

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