Nitric Acid → 1,4,7,8,9,10-Hexahydro-6-nitropyrido[3,4-f]quinoxaline-2,3-dione
Reaction equation
[NH:1]1[C:10]2[C:9]3[CH2:11][NH:12][CH2:13][CH2:14][C:8]=3[CH:7]=[CH:6][C:5]=2[NH:4][C:3](=[O:15])[C:2]1=[O:16].[N+:17]([O-])([OH:19])=[O:18]>FC(F)(F)C(O)=O>[N+:17]([C:7]1[C:8]2[CH2:14][CH2:13][NH:12][CH2:11][C:9]=2[C:10]2[NH:1][C:2](=[O:16])[C:3](=[O:15])[NH:4][C:5]=2[CH:6]=1)([O-:19])=[O:18]Participants
4
Procedure
A solution of the quinoxalinedione from Example 30 (50 mg, 0.23 mmol) in 2 mL of trifluoroacetic acid was treated with fuming nitric acid (0.1 mL, 2.3 mmol) and stirred under a nitrogen atmosphere for 19 h. After evaporating to dryness, the residue was triturated with acetone and the precipitant collected by filtration. The solid was suspended in water, heated on a hot plate and basified to pH 8 with an ammonium hydroxide solution. The solid was collected by filtration while hot, and dried in vacuo to give a yellow solid (35 mg, 65% yield). mp=245-240° C.