3-Methoxy-2-nitrobenzamide → 2-Amino-3-methoxybenzamide

HRID 374778Notes

Reaction equation

HRID 374778 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:12]([O-])=O)=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH2:8])=[O:7]>C(O)C.[Ni]>[NH2:12][C:4]1[C:3]([O:2][CH3:1])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7]

Participants

4

Reactant 1

HCID 12744933-Methoxy-2-nitrobenzamide

Product 1

HCID 185365712-Amino-3-methoxybenzamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

3-Methoxy-2-nitrobenzamide (7.0 g, 0.038 mol) was dissolved in ethanol (150 ml) and the solution stirred with Raney nickel catalyst (0.5 g) under a hydrogen atmosphere at 50 p.s.i. (3.45 bar) for 4 hours. The catalyst was removed by filtration and the solvent removed by evaporation under vacuum to give the title compound, after crystallization from ethyl acetatehexane, as a colorless solid (6.3 g, 83%), m.p. 140°-141° C. Found: C,58.03; H,6.06; N,16.65. C8H10N2O2 requires C,57.82; H,6.07; N,16.86%.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent removed by evaporation under vacuum

Sources & evidence

ORD record
ord-c9150bbec0504b97a3cbc68776470579
Source dataset
uspto-grants-1996_01
Patent number
US05482941

Reaction notes

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