Ammonium Chloride → 3-Fluoro-4-(2-methoxyethoxy)aniline

HRID 1837339Notes

Reaction equation

HRID 1837339 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][O:14][CH3:15].[Cl-].[NH4+]>C(O)C.O.[Fe]>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][O:14][CH3:15])[NH2:8]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 234980752-Fluoro-1-(2-methoxyethoxy)-4-nitrobenzene

Product 1

HCID 234981173-Fluoro-4-(2-methoxyethoxy)anilineYield 91.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-fluoro-1-(2-methoxyethoxy)-4-nitrobenzene (12.0 g , 55.7 mmol), iron powder (10.3 g, 180 mmol) and ammonium chloride (14.5 g , 270 mmol) in 170 mL of ethanol and 50 mL of water is heated at reflux for 1.5 hours then filtered hot through a pad of Diatomaceous earth, washing with ethanol. The filtrate is cooled to room temperature and the precipitated solids are removed by filtration. The filtrate is concentrated to a small volume and partitioned between ethyl acetate and water. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo to provide 9.45 g of 3-fluoro-4-(2-methoxyethoxy)aniline as a brown liquid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1.5 hours
  3. filtrationthen filtered hot through a pad of Diatomaceous earth
  4. washwashing with ethanol
  5. customthe precipitated solids are removed by filtration
  6. concentrationThe filtrate is concentrated to a small volume
  7. custompartitioned between ethyl acetate and water
  8. dry with materialThe organic layer is dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0461f0d157f2458986f680b1c611cc95
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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