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

HRID 461214Notes

Reaction equation

HRID 461214 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-54e92bf0b4d34c248565a27d94b58c91
Source dataset
uspto-grants-1977_12
Patent number
US04061791

Reaction notes

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