Diethyl Oxalate → 1,4-Dihydrobenzo[g]quinoxaline-2,3-dione

HRID 1186452

Reaction equation

[C:1]([O:8]CC)(=O)[C:2]([O:4]CC)=O.[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13]([NH2:21])[C:12]=1[NH2:22]>FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.O>[NH:21]1[C:13]2[CH:14]=[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]3=[CH:11][C:12]=2[NH:22][C:1](=[O:8])[C:2]1=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

According to Step 1 of Reference Example 10-3, diethyl oxalate (3.4 mL, 25 mmol) and ytterbium trifluoromethanesulfonate (196 mg, 0.32 mmol) were added to naphthalene-2,3-diamine (1.0 g, 6.3 mmol) and the mixture was stirred at 80° C. for 2 hours. After water was added to the reaction mixture, the precipitate was washed with ethanol. Thus, benzo[g]quinoxaline-2,3(1H,4H)-dione (1.4 g, yield: 99%) was obtained.

Workup

washthe precipitate was washed with ethanol

Sources & evidence

ORD record: ord-b3f629ad8d2c47a883a943755f96ca3f
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673908B2

Linked notes

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