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

HRID 2116544Notes

Reaction equation

HRID 2116544 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-68b4f232988e4d75a33c799ee1b6b8ce
Source dataset
uspto-grants-2008_10
Patent number
US07439242B2

Reaction notes

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