Ammonium Chloride → 5-((2-Chloropyridin-4-yl)oxy)-6-ethylpyridin-2-amine

HRID 2278902Notes

Reaction equation

HRID 2278902 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH2:18][CH3:19])=[N:11][C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[NH4+].[Cl-]>CO.C1COCC1.[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][C:10]=2[CH2:18][CH3:19])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 904031083-((2-Chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine

Product 1

HCID 904264305-((2-Chloropyridin-4-yl)oxy)-6-ethylpyridin-2-amineYield 94.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of Example A8 (1.3 g, 4.65 mmol) and NH4Cl (7.5 g, 140 mmol) in MeOH (24 mL) and THF (24 mL) was treated portion-wise with zinc dust (3 g, 45.9 mmol) and stirred at RT overnight. The solids were removed via filtration through diatomaceous earth and the filtrate concentrated to dryness to afford 5-((2-chloropyridin-4-yl)oxy)-6-ethylpyridin-2-amine (1.1 g, 85%). MS (ESI) m/z: 250.1 (M+H+).

Workup

  1. customThe solids were removed via filtration through diatomaceous earth
  2. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-677f7aa73e094fdfa08a6b5c79957b7a
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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