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

HRID 2278917Notes

Reaction equation

HRID 2278917 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.[NH4+].[Cl-]>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]([CH:11]=1)[NH2:16]

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

A mixture of 2-chloro-4-(2-chloro-5-fluoro-4-nitrophenoxy)pyridine (1.306 g, 4.31 mmol) and NH4Cl (2.305 g, 43.1 mmol) in THF (108 mL) and MeOH (108 mL) was treated with zinc dust (2.82 g, 43.1 mmol) and stirred at RT for 1 h. The solids were removed via filtration through diatomaceous earth and the filtrate concentrated under reduced pressure to afford 5-chloro-4-((2-chloropyridin-4-yl)oxy)-2-fluoroaniline (100% yield assumed) as a brown solid which was used without purification. MS (ESI) m/z: 273.0 (M+H+).

Workup

  1. customThe solids were removed via filtration through diatomaceous earth
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-6a75db85641542ff845c6064fad16d46
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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