Hydrogen Peroxide → 1-Methyl-1,4-dihydro-2,3-quinoxalinedione

HRID 1730269Notes

Reaction equation

HRID 1730269 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]1=[O:12].[OH:13]O>C(O)(=O)C>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:13])[C:3]1=[O:12]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 3514291-Methyl-1,2-dihydroquinoxalin-2-one

Product 1

HCID 6006271-Methyl-1,4-dihydro-2,3-quinoxalinedione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-Methyl-2(1H)-quinoxalinone (5.3 grams) was allowed to stand at room temperature for 72 hours in a mixture of 60 ml. of acetic acid and 35 ml. of 30 percent hydrogen peroxide. The product separated out as needles after 48 hours. After 72 hours, no starting material was detectable in thesupernatant liquid by TLC (ethyl acetate). The product was separated and washed sequentially with water and with ethanol, m.p. 287°-289° C. It was then recrystallized from water, 287°-290° C. (literature: 286°-287° C., G. W. H. Cheeseman, J. Chem. Soc. 1804 (1955); 285°-286° C., G. W.H. Cheeseman, J. Chem. Soc. 1246 (1961)). NMR also confirmed the identity of the product.

Workup

  1. additionto stand at room temperature for 72 hours in a mixture of 60 ml
  2. customThe product separated out as needles after 48 hours
  3. customThe product was separated
  4. washwashed sequentially with water and with ethanol, m.p. 287°-289° C
  5. customIt was then recrystallized from water, 287°-290° C. (literature: 286°-287° C., G. W. H. Cheeseman, J. Chem. Soc. 1804 (1955); 285°-286° C., G. W.H. Cheeseman, J. Chem. Soc. 1246 (1961))

Sources & evidence

ORD record
ord-30a8caf2dc5842e7bad6efc86bf393d0
Source dataset
uspto-grants-1976_11
Patent number
US03992378

Reaction notes

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