3,5-Dinitrobenzamide → 3,5-diaminobenzamide

HRID 1730675Notes

Reaction equation

HRID 1730675 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-86b25c5fca3443cf94c2c1857fde10eb
Source dataset
uspto-grants-1976_11
Patent number
US03993679

Reaction notes

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