Methanol → 1-methoxycarbonylmethylquinoxaline-2,3(1H,4H)-dione

HRID 1709223

Reaction equation

HRID 1709223 reaction equation
[C:1]([CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7](=[O:15])[C:6]1=[O:16])([OH:3])=[O:2].[CH3:17]O.S(=O)(=O)(O)O>O>[CH3:17][O:2][C:1]([CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7](=[O:15])[C:6]1=[O:16])=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 129386642-(2,3-Dioxo-1,2,3,4-tetrahydroquinoxalin-1-yl)acetic acid

Product 1

HCID 129386651-methoxycarbonylmethylquinoxaline-2,3(1H,4H)-dioneYield 21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.0 g (4,5 mmol) 1-carboxymethylquinoxaline-2,3(1H,4H)-dione, 15 ml dry methanol and 0,2 ml concentrated sulfuric acid was stirred at 80° C. for 1 h. After cooling to 25° C. the reaction mixture was poured in water and made alkaline. The precipitate was filtered off and recrystallized (acetone) to give 0.22 g (21%) 1-methoxycarbonylmethylquinoxaline-2,3(1H,4H)-dione. M.p. 269° C. 1H-NMR (DMSO-d6 ): 12.0 (1H, broad s), 7.1 (4H, s), 4.9 (2H, s), 3.7 (3H, s).

Workup

  1. temperatureAfter cooling to 25° C. the reaction mixture
  2. filtrationThe precipitate was filtered off
  3. customrecrystallized (acetone)

Sources & evidence

ORD record
ord-4639ed60cc8e4cc09cbec31fc2d78fbb
Source dataset
uspto-grants-1990_08
Patent number
US04948794

Linked notes

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