Benzamide, 3-nitro-N-(3-nitrophenyl)- → Benzamide, 3-amino-N-(3-aminophenyl)-

HRID 65610Notes

Reaction equation

HRID 65610 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][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>[NH2:1][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][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 66861Benzamide, 3-nitro-N-(3-nitrophenyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 66859Benzamide, 3-amino-N-(3-aminophenyl)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 14.3 g of 3,3'-dinitrobenzanilide in 150 ml. of dioxane is hydrogenated at three atmospheres of hydrogen using 1 g. of 10% palladium-on-charcoal catalyst. The catalyst is removed by filtration and the filtrate evaporated to dryness. The residue is recrystallized from ethanol. There is obtained 8.72 g. of material melting at 123°-4°.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe filtrate evaporated to dryness
  3. customThe residue is recrystallized from ethanol
  4. customThere is obtained 8.72 g

Sources & evidence

ORD record
ord-4e2946f77f2c40ab8b38465e36dfb128
Source dataset
uspto-grants-1978_12
Patent number
US04128570

Reaction notes

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