Stannous Chloride → 5-(4-Aminophenoxy)-3-chloropyridine

HRID 1531996Notes

Reaction equation

HRID 1531996 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:10]=[C:11]([Cl:15])[CH:12]=[N:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.Cl[Sn]Cl>CCO>[NH2:1][C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:10]=[C:11]([Cl:15])[CH:12]=[N:13][CH:14]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 121093595-(4-Nitrophenoxy)-3-chloropyridine

Product 1

HCID 121093605-(4-Aminophenoxy)-3-chloropyridineYield 97.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 5-(4-nitrophenoxy)-3-chloropyridine (219 mg, 0.873 mmol) in EtOH (4 mL) was added SnCl2 (730 mg, 3.24 mmol). The solution was refluxed for 1.25 hr and the solvent was removed by evaporation. The resulting crude solid was purified by chromatography (97.5:2.5 CH2Cl2:MeOH) to provide 187.7 mg (78% yield) of the title compound.

Workup

  1. temperatureThe solution was refluxed for 1.25 hr
  2. customthe solvent was removed by evaporation
  3. customThe resulting crude solid was purified by chromatography (97.5:2.5 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-e5a927a7149a43429c6a3b4078114ffd
Source dataset
uspto-grants-2001_03
Patent number
US06200995B1

Reaction notes

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