N-(5-chloropyridin-2-yl)-2-nitrobenzamide → 2-amino-N-(5-chloropyridin-2-yl)benzamide

HRID 1372873Notes

Reaction equation

HRID 1372873 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-])=O)=[N:6][CH:7]=1>C1COCC1.C(OCC)(=O)C.[Ni]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])=[N:6][CH:7]=1

Participants

5

Reactant 1

HCID 766647N-(5-chloropyridin-2-yl)-2-nitrobenzamide

Product 1

HCID 219063812-amino-N-(5-chloropyridin-2-yl)benzamideYield 84.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(5-chloropyridin-2-yl)-2-nitrobenzamide (2 g, 7.2 mmol) in THF (50 mL) and ethyl acetate (50 mL) was added Raney Ni (0.2 g) and the mixture was placed under hydrogen (4.1 bar) in a high pressure apparatus. After shaking overnight, the mixture was filtered and concentrated in vacuo and purified by flash chromatography to give 1.5 g (83%) of an off-white solid.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-9b290d510e8d483f88a78fa4b5852741
Source dataset
uspto-grants-2007_01
Patent number
US07160878B2

Reaction notes

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