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

HRID 427712Notes

Reaction equation

HRID 427712 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-49ab1e75f4764ea1903f26b672d22b5b
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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