3,5-Dinitrobenzamide → 3,5-diaminobenzamide

HRID 372244Notes

Reaction equation

HRID 372244 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-f05e2870bbd34c65958ae8e8f4ddbb53
Source dataset
uspto-grants-1978_05
Patent number
US04089973

Reaction notes

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