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

HRID 2060695Notes

Reaction equation

HRID 2060695 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 (1.306 g, 4.31 mmol) was dissolved in THF (108 ml) and MeOH (108 ml). Ammonium chloride (2.305 g, 43.1 mmol) was then added, followed by zinc dust (2.82 g, 43.1 mmol). The reaction mixture was stirred for 1 hour at RT. The solids were filtered over Celite® and the solution 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 over Celite®
  2. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-88e54b5c1f19418e9c97f3728fedde32
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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