1-Phenyl-1,2-propanedione → 2-Methyl-6,7-dinitro-3-phenylquinoxaline
Reaction equation
[N+:1]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([NH2:13])=[C:6]([NH2:14])[CH:5]=1)([O-:3])=[O:2].[C:15]1([C:21](=O)[C:22](=O)[CH3:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[CH3:23][C:22]1[C:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:14][C:6]2[C:7](=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4,5-Dinitro-1,2-phenylenediamine (890 mg, 4.5 mmol) (G. W. H. Cheeseman, J. Org. Soc. 1170-5, 1962) was mixed with 1-phenyl-1,2-propanedione (800 mg, 5.4 mmol) in ethanol (18 ml). The mixture was heated to reflux for 4 hours. The ethanol was removed by evaporation and the remaining brown oil was suspended in dichloromethane (20 ml). Purification by column chromatography on silica gel eluting with dichloromethane followed by recrystallisation from ethanol yielded the title compound (200 mg, 14%).