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

HRID 65612Notes

Reaction equation

HRID 65612 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-14dbbd04960841d7b3e26d55be517ba3
Source dataset
uspto-grants-1978_12
Patent number
US04128570

Reaction notes

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