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

HRID 1403604Notes

Reaction equation

HRID 1403604 reaction equation
[Cl:1][C:2]1[C:3](=[O:26])[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]([F:16])[CH:6]=2.S(=O)(=O)(O)O>>[Cl:1][C:2]1[C:3](=[O:26])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([F:16])[CH:6]=2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 70665073Methyl 3-chloro-7-fluoro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Product 1

HCID 70665231Methyl 3-chloro-7-fluoro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Procedure

Methyl 3-chloro-7-fluoro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (4.0 g, 10.62 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-fluoro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a yellow solid (2.0 g, crude), which was used in the next step without further purification.

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-eeca9bac6ff143499f4298a8ae3cd9aa
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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