Diethyl Oxalate → Methyl 7-fluoro-1-(4-methoxybenzyl)-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

HRID 1403602Notes

Reaction equation

HRID 1403602 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:4][C:5]([F:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:23](OCC)(=[O:29])[C:24](OCC)=[O:25]>CCOCC>[F:12][C:5]1[CH:4]=[C:3]2[C:2]([NH:1][C:23](=[O:29])[C:24](=[O:25])[N:13]2[CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 70665225Methyl 5-amino-2-fluoro-4-(4-methoxybenzylamino)benzoate

Product 1

HCID 70664935Methyl 7-fluoro-1-(4-methoxybenzyl)-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The solution of methyl 5-amino-2-fluoro-4-(4-methoxybenzylamino)benzoate (30 g, 98.58 mmol) in diethyl oxalate (100 ml) was stirred for 3 h at reflux and then cooled with a water/ice bath, diluted with ether (500 ml). The product was collected by filtration to afford methyl 7-fluoro-1-(4-methoxybenzyl)-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate as a light yellow solid (35.0 g, 99%).

Workup

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

Sources & evidence

ORD record
ord-31cfae4bad9649daadf391a9b0c4ccf7
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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