Sulfuric Acid → Methyl 3-chloro-7-methoxy-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403589Notes

Reaction equation

HRID 1403589 reaction equation
[Cl:1][C:2]1[C:3](=[O:27])[N:4](CC2C=CC(OC)=CC=2)[C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([O:16][CH3:17])[CH:6]=2.S(=O)(=O)(O)O>>[Cl:1][C:2]1[C:3](=[O:27])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([O:16][CH3:17])[CH:6]=2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 70664997Methyl 3-chloro-7-methoxy-1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Product 1

HCID 70665121Methyl 3-chloro-7-methoxy-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Procedure

Methyl 3-chloro-7-methoxy-1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (6.0 g, 15.43 mmol) was added to sulfuric acid (conc, 15 mL) in several batches with stirring at room temperature and then stirred for 10 minutes. The resulting solution was diluted with ice-water (100 mL) and extracted with ethyl acetate (3×200 mL). The organic layers were combined and dried over anhydrous magnesium sulfate and concentrated in vacuo to afford methyl 3-chloro-7-methoxy-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a yellow solid (2.5, 60%).

Workup

  1. stirringstirred for 10 minutes
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b8f987a25734c15b1c1736f3f3a043e
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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