3,5-Dinitrobenzamide → 3,5-diaminobenzamide

HRID 236932Notes

Reaction equation

HRID 236932 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-])=O)[CH:12]=1)[C:7]([NH2:9])=[O:8])([O-])=O.[H][H]>[Pd].C(OCC)(=O)C.C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([NH2:13])[CH:12]=1)[C:7]([NH2:9])=[O:8]

Participants

5

Reactant 2

HCID 45113,5-DinitrobenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 115137753,5-diaminobenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of 20.5 gm. (0.097 mole) of 3,5-dinitrobenzamide in 450 ml. of an ethyl acetate-ethanol mixture (2:1) is hydrogenated at 3 atmospheres of hydrogen using 1 gm. of 10% palladium on charcoal as catalyst. When absorption of hydrogen is complete, the catalyst is removed by filtration and the filtrate is concentrated to dryness under reduced pressure and the residue recrystallized from water. There is obtained 11.65 gm. (79% of long yellow needles melting at 108°-9°.

Workup

  1. customWhen absorption of hydrogen
  2. customthe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure
  4. customthe residue recrystallized from water
  5. customThere is obtained 11.65 gm

Sources & evidence

ORD record
ord-34d78c8d9d5f48a59f754d0678f0c446
Source dataset
uspto-grants-1979_06
Patent number
US04159278

Reaction notes

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