Diethyl Oxalate → Methyl 7-methoxy-1-[(4-methoxyphenyl)methyl]-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

HRID 1403587Notes

Reaction equation

HRID 1403587 reaction equation
[NH2:1][C:2]1[C:3]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:24](OCC)(=[O:30])[C:25](OCC)=[O:26]>CCOCC>[CH3:13][O:12][C:5]1[CH:4]=[C:3]2[C:2]([NH:1][C:24](=[O:30])[C:25](=[O:26])[N:14]2[CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 70664744Methyl 5-amino-2-methoxy-4-(4-methoxybenzylamino)benzoate

Product 1

HCID 70664938Methyl 7-methoxy-1-[(4-methoxyphenyl)methyl]-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylateYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The solution of methyl 5-amino-2-methoxy-4-(4-methoxybenzylamino)benzoate (30 g, 94.83 mmol) in 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). The product was collected by filtration to afford methyl 7-methoxy-1-[(4-methoxyphenyl)methyl]-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate as a light yellow solid (25.0 g, 71%).

Workup

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

Sources & evidence

ORD record
ord-d89e689956614693a34166332cf10aeb
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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