Ammonium Chloride → 4-Chloro-3,5-bis(pyridin-3-yloxy)-benzene-1,2-diamine

HRID 13257Notes

Reaction equation

HRID 13257 reaction equation
[Cl-].[NH4+].[Cl:3][C:4]1[C:5]([O:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[C:6]([C:8]([N+:18]([O-])=O)=[CH:9][C:10]=1[O:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[NH2:7]>CO.O.[Fe]>[Cl:3][C:4]1[C:5]([O:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[C:6]([NH2:7])[C:8]([NH2:18])=[CH:9][C:10]=1[O:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 231457143-Chloro-2,4-bis(pyridin-3-yloxy)-6-nitroaniline

Product 1

HCID 231451794-Chloro-3,5-bis(pyridin-3-yloxy)-benzene-1,2-diamine

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

128 mg of ammonium chloride and 67 mg of iron powder were added to a suspension of 143 mg of 3-chloro-2,4-bis(pyridin-3-yloxy)-6-nitroaniline in 8 ml of methanol and 4 ml of water, and the reaction liquid was heated under reflux for 2 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 to obtain the entitled compound as a pale brown solid.

Workup

  1. customthe reaction liquid
  2. temperaturewas heated
  3. temperatureunder reflux for 2 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

Sources & evidence

ORD record
ord-a6ce796d8a5a4700b1daae1a73a2e44f
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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