Pyruvic Acid → 7-Methoxy-3-methylquinoxalin-2(1H)-one

HRID 1019963Notes

Reaction equation

HRID 1019963 reaction equation
[C:1](O)(=[O:5])[C:2]([CH3:4])=O.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([NH2:16])[C:12]([NH2:15])=[CH:13][CH:14]=1.[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:12]([N:15]=[C:2]([CH3:4])[C:1](=[O:5])[NH:16]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 1060Pyruvic AcidHCID 14798Sodium HydroxideHCID 1534044-Methoxy-o-phenylenediamine

Product 1

HCID 217964227-Methoxy-3-methylquinoxalin-2(1H)-oneYield 91%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Pyruvic acid (60 mL, 868 mmol, 1.2 eq) is added at room temperature to a stirred suspension of 4-methoxy-benzene-1,2-diamine (100 g, 724 mmol, 1.0 eq) in 1.8M sulfuric acid aqueous solution (1000 mL). After 24 hours stirring at room temperature, the reaction mixture is neutralized by the addition of 1N sodium hydroxide aqueous solution. The resulting precipitate is filtered and washed with water to afford 7-methoxy-3-methyl-1H-quinoxalin-2-one as a dark purple solid (125 g, 91% yield).

Workup

  1. filtrationThe resulting precipitate is filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-ec841673835441679fbf65ded3e108f6
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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