5-Chloro-2-nitro-n-(2-pyridyl)benzamide → 2-Amino-5-chloro-N-2-pyridinylbenzamide

HRID 395862Notes

Reaction equation

HRID 395862 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-])=O)=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:8]>C1COCC1.C(OCC)(=O)C.[Ni]>[NH2:17][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:16][C:6]=1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:8]

Participants

5

Reactant 1

HCID 46196505-Chloro-2-nitro-n-(2-pyridyl)benzamide

Product 1

HCID 121506942-Amino-5-chloro-N-2-pyridinylbenzamideYield 67.3%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-2-nitro-N-(2-pyridyl)benzamide (4 g, 14.4 mmol) in THF (50 mL) and ethyl acetate (50 mL) was added Raney nickel (0.5 g). The mixture was placed under an atmosphere of hydrogen (4.1 bar) overnight. The mixture was then filtered and the filtrate was flushed through a pad of silica gel, eluting with ethyl acetate, and then concentrated in vacuo. The crude solid was suspended in diethyl ether, sonicated, filtered and dried in vacuo to give 2.4 g (67%) of a faint green solid.

Workup

  1. filtrationThe mixture was then filtered
  2. customthe filtrate was flushed through a pad of silica gel
  3. washeluting with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customsonicated
  6. filtrationfiltered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-25c8482337784a1281f368af2c822003
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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