2-Nitrobenzene-1,3-dicarboxamide → 2-Aminobenzene-1,3-dicarboxamide

HRID 412043Notes

Reaction equation

HRID 412043 reaction equation
[C:1]([C:4]1[C:5]([N+:13]([O-])=O)=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH2:9])=[O:8])(=[O:3])[NH2:2]>C(O)C.[Pd]>[NH2:13][C:5]1[C:6]([C:7](=[O:8])[NH2:9])=[CH:10][CH:11]=[CH:12][C:4]=1[C:1]([NH2:2])=[O:3]

Participants

4

Reactant 1

HCID 141474892-Nitrobenzene-1,3-dicarboxamide

Product 1

HCID 102413842-Aminobenzene-1,3-dicarboxamideYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Carbamoyl-2-nitrobenzamide (0.6 g, 0.0029 mol) was dissolved in ethanol (50 ml) and the solution stirred with 5% palladium on charcoal catalyst (0.1 g) under a hydrogen atmosphere at 50 p.s.i. (3.45 bar) and 50° C. for 5 hours. The catalyst was removed by filtration, the solvent evaporated under vacuum and the residue crystallized from water to give the title compound as a grey solid (0.26 g, 50%), m.p. 284-288° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated under vacuum
  3. customthe residue crystallized from water

Sources & evidence

ORD record
ord-46a0a374b11943eb824c8dd92a700227
Source dataset
uspto-grants-2003_05
Patent number
US06562830B1

Reaction notes

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