Ammonium Chloride → 5-(2-Chloropyridin-4-yloxy)pyridin-2-amine

HRID 2278891Notes

Reaction equation

HRID 2278891 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.[NH4+].[Cl-]>C1COCC1.CO.[Zn]>[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

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 593227792-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine

Product 1

HCID 593227885-(2-Chloropyridin-4-yloxy)pyridin-2-amineYield 63%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example A1 (2.55 g, 10.13 mmol) and NH4Cl (5.42 g, 101 mmol) in THF (250 mL) and MeOH (250 mL) was treated with zinc dust (6.63 g, 101 mmol), stirred at RT for 3 h, the solids removed via filtration and the filtrate concentrated to dryness and purified by silica gel chromatography to provide 5-((2-chloropyridin-4-yl)oxy)pyridin-2-amine (1.41 g, 63% yield).

Workup

  1. customthe solids removed via filtration
  2. concentrationthe filtrate concentrated to dryness
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-2fb7f15f0279428bb309df43ed1be4a5
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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