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

HRID 1520135Notes

Reaction equation

HRID 1520135 reaction equation
[Cl:1][C:2]1[C:3](=[O:25])[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])=[CH:7][CH:6]=2.S(=O)(=O)(O)O>>[Cl:1][C:2]1[C:3](=[O:25])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 68194043HCID 68194043, compound

Product 1

HCID 68194304Methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Procedure

Methyl 3-chloro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (13 g, 36.31 mmol) was added to sulfuric acid (conc, 15 ml) in several batches with stirring at room temperature and then stirred an additional 10 mins. The resulting solution was quenched with ice-water (100 ml), adjusted to PH=7 with aqueous sodium hydroxide (10 N), and extracted with 1-butanol (3×200 ml). The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a yellow solid (12.4 g, crude).

Workup

  1. stirringstirred an additional 10 mins
  2. customThe resulting solution was quenched with ice-water (100 ml)
  3. extractionextracted with 1-butanol (3×200 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c43691b3f0384a1e89e17d554cfbdb67
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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