Ammonium Chloride → HCID 22117702, compound

HRID 1275683Notes

Reaction equation

HRID 1275683 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:5][O:6][C:7]1[CH:22]=[CH:21][C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-])=O)=[CH:9][CH:8]=1.[Cl-:27].[NH4+]>C(O)C.O.[Fe]>[ClH:27].[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:5][O:6][C:7]1[CH:22]=[CH:21][C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[CH:9][CH:8]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 15480990HCID 15480990, compound

Product 1

HCID 22117702HCID 22117702, compoundYield 148.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-[4-(3,4-difluorobenzyloxy)phenoxy]-2-nitrobenzene (0.96 g, 2.7 mmol) in ethanol (50 ml) were an iron powder (0.75 g, 13.4 mg-atom) and a solution of ammonium chloride (0.09 g, 1.7 mmol) in water (10 ml), followed by reflux for 3 hours. The reaction solution was cooled to room temperature, and after removal of the insoluble matter by filtration, the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and dried over magnesium sulfate. After removal of the drying agent, 4 N hydrogen chloride-ethyl acetate solution (2 ml) was added, followed by stirring for 30 minutes. The precipitated crystals were collected by filtration and dried to give the title compound (0.92 g).

Workup

  1. temperatureby reflux for 3 hours
  2. customafter removal of the insoluble matter
  3. filtrationby filtration
  4. customthe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. customAfter removal of the drying agent, 4 N hydrogen chloride-ethyl acetate solution (2 ml)
  8. additionwas added
  9. filtrationThe precipitated crystals were collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-1cbcdc0491f2406caa7dc2638e02660b
Source dataset
uspto-grants-2000_12
Patent number
US06162832

Reaction notes

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