3,5-dinitro-N-(3-nitrophenyl)benzamide → 3,3',5-Triaminobenzanilide
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[C:20]([N+:22]([O-])=O)[CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1)=[O:8])([O-])=O.[H][H]>[Pd].O1CCOCC1>[NH2:22][C:20]1[CH:19]=[C:6]([CH:5]=[C:4]([NH2:1])[CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1)=[O:8]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 13.29 gm. (0.04 mole) of 3,3',5-trinitrobenzanilide in 150 ml. of dioxane is hydrogenated at three atmospheres of hydrogen using 1 gm. of 10% palladium-on-charcoal catalyst. The catalyst is removed by filtration, the filtrate evaporated to dryness under reduced pressure, and the residue dried by distilling 200 ml. of benzene from the reaction mixture.