2-Chloro-4-methyl-5-nitropyridine → 3-Amino-6-chloro-4-picoline

HRID 902886Notes

Reaction equation

HRID 902886 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1>C(O)C.[Ni]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([NH2:9])=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 1

HCID 3453642-Chloro-4-methyl-5-nitropyridine

Product 1

HCID 27344253-Amino-6-chloro-4-picolineYield 79.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

2-Chloro-4-methyl-5-nitropyridine (173 mg) was dissolved in ethanol (5 ml), and a catalytic amount of Raney nickel catalyst was added to stir the mixture at room temperature for 9 hours under a hydrogen atmosphere. The catalyst was removed by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2) to obtain the title compound (113 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-704524813c904ac5a9c6261baa3413cf
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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