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

HRID 1422798Notes

Reaction equation

HRID 1422798 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-be62cb531c8f46d0b64dc84ddba8d8ef
Source dataset
uspto-grants-2015_01
Patent number
US08927542B2

Reaction notes

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