Ammonium Chloride → 5-Chloro-4-(2-chloropyridin-4-yloxy)-2-fluorobenzenamine

HRID 1411134Notes

Reaction equation

HRID 1411134 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[C:13]([F:15])[C:12]([N+:16]([O-])=O)=[CH:11][C:10]=2[Cl:19])[CH:5]=[CH:4][N:3]=1.[Cl-].[NH4+]>C1COCC1.CO.[Zn]>[Cl:19][C:10]1[C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)=[CH:14][C:13]([F:15])=[C:12]([NH2:16])[CH:11]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 866416872-Chloro-4-(2-chloro-5-fluoro-4-nitrophenoxy)pyridine

Product 1

HCID 866416885-Chloro-4-(2-chloropyridin-4-yloxy)-2-fluorobenzenamineYield 100%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-4-(2-chloro-5-fluoro-4-nitrophenoxy)pyridine (1.31 g, 4.31 mmol) was dissolved in THF (108 mL) and MeOH (108 mL). Ammonium chloride (2.31 g, 43.1 mmol) was added, followed by zinc dust (2.82 g, 43.1 mmol). The reaction mixture was stirred at RT for 1 h. The solids were filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure to yield 5-chloro-4-(2-chloropyridin-4-yloxy)-2-fluorobenzenamine as a brown solid which was used without purification assuming a 100% yield. MS (ESI) m/z: 273.0 (M+H+).

Workup

  1. filtrationThe solids were filtered through diatomaceous earth
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6f52b4ec18a343489e7df952f3316961
Source dataset
uspto-grants-2014_12
Patent number
US08921565B2

Reaction notes

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