Ammonium Chloride → 2-(4-Fluoro-2-methoxyphenoxy)aniline

HRID 1946584Notes

Reaction equation

HRID 1946584 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)=[C:4]([O:18][CH3:19])[CH:3]=1.[Cl-].[NH4+]>CO.O.[Cl-].[Zn+2].[Cl-]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])=[C:4]([O:18][CH3:19])[CH:3]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 597837514-Fluoro-2-methoxy-1-(2-nitrophenoxy)benzene

Product 1

HCID 597837992-(4-Fluoro-2-methoxyphenoxy)anilineYield 100.5%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of title compound 90 (9.32 g, 35.4 mmol) in MeOH (30 mL) and water (5 mL) was added ammonium chloride (3.79 g, 70.8 mmol) and zinc chloride (20.83 g, 319 mmol) and the reaction mixture was heated to reflux for 2 hours. The mixture was cooled to room temperature and filtered and the solvent removed. The residue was diluted with ethyl acetate and water and the organic phase was washed well with water, dried over Na2SO4, filtered and concentrated to afford title compound 91 (8.3 g, 100%). LRMS (ESI): (calc) 233.09 (found) 234.1 (MH)+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationfiltered
  4. customthe solvent removed
  5. additionThe residue was diluted with ethyl acetate and water
  6. washthe organic phase was washed well with water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3c2e21cde6e44a7ba8591dd97b57943d
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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