3,5-Dinitrobenzamide → 3,5-diaminobenzamide

HRID 2052591Notes

Reaction equation

HRID 2052591 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 of 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 108-0°.

Workup

  1. customWhen absorption of hydrogen
  2. customthe catalyst is removed of 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-5a3728245fbf4106acaea43a0953d39d
Source dataset
uspto-grants-1980_01
Patent number
US04186127

Reaction notes

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