2-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine → 5-(2-Chloropyridin-4-yloxy)pyridin-2-amine

HRID 709965Notes

Reaction equation

HRID 709965 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1>CO.[Ni]>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[N:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 593227792-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine

Product 1

HCID 593227885-(2-Chloropyridin-4-yloxy)pyridin-2-amineYield 105.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-chloro-4-((6-nitropyridin-3-yl)oxy)pyridine (20.0 g, 79 mmol) in MeOH (40 mL) was hydrogenated in presence of Raney Nickel (2.00 g, 34.1 mmol) at 40 psi for 3 h. The catalyst was removed via filtration, rinsed with MeOH and the filtrate concentrated to dryness to afford 5-((2-chloropyridin-4-yl)oxy)pyridin-2-amine (18.52 g, 105%) as a brown solid. MS (ESI) m/z: 222.0 (M+H+).

Workup

  1. customThe catalyst was removed via filtration
  2. washrinsed with MeOH
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-ddd739c9f1204cf885f3409b2c36c287
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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