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

HRID 2104418Notes

Reaction equation

HRID 2104418 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1.[H][H]>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

5

Reactant 2

HCID 3453642-Chloro-4-methyl-5-nitropyridineHCID 178418361HCID 178418361, compound

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). To the solution, a catalytic amount of Raney nickel was added, and the resultant mixture was stirred in a hydrogen atmosphere at room temperature for 9 hours. The catalyst was removed through filtration, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2), to thereby give the title compound (113 mg).

Workup

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

Sources & evidence

ORD record
ord-de4a2d9edc2448ddbc4b0dae651e7d1e
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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