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

HRID 2279397Notes

Reaction equation

HRID 2279397 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-086015272fe2443993ae87604f50a1a9
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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