Diethyl Oxalate → HCID 67133792, compound

Reaction equation

[CH3:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]([NH2:12])=[C:4]([NH2:13])[CH:3]=1.[C:14](OCC)(=[O:20])[C:15](OCC)=[O:16]>>[CH3:1][C:2]1[CH:3]=[C:4]2[C:5]([NH:12][C:14](=[O:20])[C:15](=[O:16])[NH:13]2)=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

Reactant 2

HCID 7268Diethyl Oxalate

HCID 585752204,5-Diamino-2-methyl-benzoic acid methyl ester

Product 1

HCID 67133792HCID 67133792, compound

Conditions

Temperature: 145 °C

Procedure

A mixture of 3.98 g of methyl 4,5-diamino-2-methyl benzoate and 40 mL of diethyl oxalate was stirred at 145° C. for 3 hours. After cooling to room temperature, the solid was collected by filtration, washed with diethyl ether, and dried under reduced pressure to obtain 4.75 g of methyl 7-methyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate.

Workup

temperatureAfter cooling to room temperature
filtrationthe solid was collected by filtration
washwashed with diethyl ether
customdried under reduced pressure

Sources & evidence

ORD record: ord-92c27bd6dd8d4b0fa81edd4957b549c1
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901126B2

Reaction notes

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