3,5-dinitro-N-(3-nitrophenyl)benzamide → 3,3',5-Triaminobenzanilide

HRID 263055Notes

Reaction equation

HRID 263055 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

HCID 30945643,5-dinitro-N-(3-nitrophenyl)benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 213150323,3',5-Triaminobenzanilide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

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.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe filtrate evaporated to dryness under reduced pressure
  3. customthe residue dried
  4. distillationby distilling 200 ml

Sources & evidence

ORD record
ord-36603284383343aeb5b6acbebb3285bb
Source dataset
uspto-grants-1979_05
Patent number
US04156012

Reaction notes

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