Ammonium Chloride → 3-Chloro-2,4-bis(pyridin-3-yloxy)aniline

HRID 13255

Reaction equation

HRID 13255 reaction equation
[Cl-].[NH4+].[Cl:3][C:4]1[C:5]([O:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[C:6]([N+:17]([O-])=O)[CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1>CO.O.[Fe]>[Cl:3][C:4]1[C:5]([O:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[C:6]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[NH2:17]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 231457333-Chloro-2,4-bis(pyridin-3-yloxy)-nitrobenzene

Product 1

HCID 231456963-Chloro-2,4-bis(pyridin-3-yloxy)aniline

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

963 mg of ammonium chloride and 503 mg of iron powder were added to a suspension of 1.2 g of 3-chloro-2,4-bis(pyridin-3-yloxy)-nitrobenzene in 15 ml of methanol and 7.5 ml of water, and the reaction liquid was heated under reflux for 3 hours. The reaction liquid was filtered, and the solvent was evaporated away under reduced pressure. The residue was diluted with ethyl acetate, washed with water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified with silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1 to ethyl acetate) to obtain the entitled compound as a pale yellow oily substance.

Workup

  1. customthe reaction liquid
  2. temperaturewas heated
  3. temperatureunder reflux for 3 hours
  4. customThe reaction liquid
  5. filtrationwas filtered
  6. customthe solvent was evaporated away under reduced pressure
  7. additionThe residue was diluted with ethyl acetate
  8. washwashed with water
  9. dry with materialdried with anhydrous magnesium sulfate
  10. customThe solvent was evaporated away under reduced pressure
  11. customthe resulting residue was purified with silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1 to ethyl acetate)
  12. customto obtain the entitled compound as a pale yellow oily substance

Sources & evidence

ORD record
ord-b2bf62edf2c6442ea73ffc043f2ba1f3
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

Loading…