Methanol → Methyl 1,2,3,4-tetrahydro-6-methyl-2,3-dioxo-5-quinoxalinecarboxylate

HRID 1251006Notes

Reaction equation

HRID 1251006 reaction equation
[NH2:1][C:2]1[C:3]([NH2:12])=[C:4]([C:8]([CH3:11])=[CH:9][CH:10]=1)[C:5]([O-:7])=[O:6].[C:13](OC)(=[O:18])[C:14](OC)=[O:15].[CH3:21]O>>[CH3:11][C:8]1[CH:9]=[CH:10][C:2]2[NH:1][C:14](=[O:15])[C:13](=[O:18])[NH:12][C:3]=2[C:4]=1[C:5]([O:7][CH3:21])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 11120Dimethyl oxalateHCID 18424114HCID 18424114, compound2×

Product 1

HCID 10847279Methyl 1,2,3,4-tetrahydro-6-methyl-2,3-dioxo-5-quinoxalinecarboxylate

Procedure

A solution of 2,3-diamino-6-methylbenzoic acid, methyl ester (compound 6) (1.14 g, 6.35 mmol) and dimethyl oxalate (3.34 g, 28.5 mmol) in MeOH (30 mL) was refluxed for 6 days. Upon cooling to room temperature, the precipitated product was collected and washed with a small amount of MeOH to give 1.02 g (69%).

Workup

  1. customthe precipitated product was collected
  2. washwashed with a small amount of MeOH
  3. customto give 1.02 g (69%)

Sources & evidence

ORD record
ord-926cfc0941924c00a943d89df2e84308
Source dataset
uspto-grants-2002_01
Patent number
US06340758B1

Reaction notes

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