Ammonium Chloride → 4-(4-Chlorophenoxy)pyridin-3-amine

HRID 1642268Notes

Reaction equation

HRID 1642268 reaction equation
[Cl-].[NH4+].[Cl:3][C:4]1[CH:19]=[CH:18][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N+:15]([O-])=O)=[CH:6][CH:5]=1>C(O)C.O.[Fe]>[Cl:3][C:4]1[CH:19]=[CH:18][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[NH2:15])=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 528401924-(4-Chlorophenoxy)-3-nitropyridine

Product 1

HCID 288901544-(4-Chlorophenoxy)pyridin-3-amineYield 75%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a refluxing mixture of iron powder (1.91 g, 34.43 mmol) and ammonium chloride (230 mg, 4.30 mmol) in ethanol (45 μL) and water (8 mL) was added 4-(4-chlorophenoxy)-3-nitropyridine (AMR01116, 1.57 g, 6.26 mmol) and the resulting mixture was stirred at reflux for 1 h. After removal of the solvent, the residue was diluted in aqueous sodium hydrogen carbonate (40 mL) and extracted with DCM (3×20 mL). The organic layer was dried (MgSO4), filtered and evaporated. Flashmaster chromatography of the crude product using DCM/MeOH 9:1 as eluent gave 4-(4-chlorophenoxy)-pyridin-3-ylamin (1.03 g, 75%) as a white solid, mp 104-106° C.

Workup

  1. temperatureat reflux for 1 h
  2. customAfter removal of the solvent
  3. additionthe residue was diluted in aqueous sodium hydrogen carbonate (40 mL)
  4. extractionextracted with DCM (3×20 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c69ddf6a6ac64b37a27d8da846da1077
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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