Diethyl Oxalate → HCID 68194123, compound

HRID 1520133Notes

Reaction equation

HRID 1520133 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:5]([O:7][CH3:8])=[O:6].[C:22](OCC)(=[O:28])[C:23](OCC)=[O:24]>CCOCC>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:12]2[C:11]3[C:2](=[CH:3][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=3)[NH:1][C:23](=[O:24])[C:22]2=[O:28])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 46344397HCID 46344397, compound

Product 1

HCID 68194123HCID 68194123, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl 3-amino-4-(4-methoxybenzylamino)benzoate (3 g, 10.48 mmol) and diethyl oxalate (100 ml) was stirred for 3 h at reflux and then cooled with a water/ice bath, and diluted with ether (500 ml). Tthe product was collected by filtration to afford methyl 1-(4-methoxybenzyl)-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate as a green solid (2.64 g, 74%).

Workup

  1. temperatureat reflux
  2. temperaturecooled with a water/ice bath
  3. filtrationTthe product was collected by filtration

Sources & evidence

ORD record
ord-a5f9316f9df5497abbf90f6b14ffd533
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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