Ammonium Chloride → 3,4-Difluoro-2-methoxyaniline

HRID 358885Notes

Reaction equation

HRID 358885 reaction equation
[Cl-].[NH4+].[F:3][C:4]1[C:5]([O:14][CH3:15])=[C:6]([N+:11]([O-])=O)[CH:7]=[CH:8][C:9]=1[F:10]>CO>[F:3][C:4]1[C:5]([O:14][CH3:15])=[C:6]([CH:7]=[CH:8][C:9]=1[F:10])[NH2:11]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 27827542,3-Difluoro-6-nitroanisole

Product 1

HCID 111374253,4-Difluoro-2-methoxyanilineYield 56.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

22.6 g (0.422 mole) of ammonium chloride and 38.2 g of reduced iron were added to a solution of 23.0 g (0.114 mole) of 3,4-difluoro-2-methoxy-1-nitrobenzene (VII) [prepared as described in step (a) above] in 1 liter of 80% aqueous methanol. The mixture was then heated under reflux for 4 hours, whilst stirring. At the end of this time, the reaction mixture was filtered, and the filtrate was concentrated by evaporation under reduced pressure. The residue was extracted with toluene. The toluene extract was washed with water, dried, and concentrated by evaporation under reduced pressure to give 10.2 g of 3,4-difluoro-2-methoxyaniline (VIII) as a reddish-brown oil [Step (B2)].

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 4 hours
  3. filtrationAt the end of this time, the reaction mixture was filtered
  4. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  5. extractionThe residue was extracted with toluene
  6. extractionThe toluene extract
  7. washwas washed with water
  8. customdried
  9. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-11eff042e4f847699b69513415f89e48
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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