Diethyl Oxalate → Methyl 2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

HRID 1270157Notes

Reaction equation

HRID 1270157 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1.C([O:15][C:16](=O)[C:17](OCC)=[O:18])C>>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:8][CH:9]=1)[NH:10][C:16](=[O:15])[C:17](=[O:18])[NH:11]2)=[O:12]

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 1355243,5-Diamino-2-methylbenzoic acid

Product 1

HCID 23847563Methyl 2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

Conditions

Temperature
23 °C

Procedure

A mixture of methyl-3,4-diaminobenzoate (4.5 g) in diethyloxalate (50 mL) was heated at reflux for three hrs. After cooling to 23° C., the solid was isolated by filtration, affording 2,3-dioxo-1,2,3,4-tetrahydro-quinoxaline-6-carboxylic acid methyl ester as a light yellow solid. MS (M−H)−=219.1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for three hrs
  3. customthe solid was isolated by filtration

Sources & evidence

ORD record
ord-cec1be3dd0604c3991de92514d48098e
Source dataset
uspto-grants-2007_04
Patent number
US07202245B2

Reaction notes

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