Ammonium Chloride → 4-Bromo-3-methoxyaniline

HRID 581979Notes

Reaction equation

HRID 581979 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[O:11][CH3:12].[Cl-].[NH4+]>CO.O.[Fe]>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:2]=1[Br:1])[NH2:8]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 1012932-Bromo-5-nitroanisole

Product 1

HCID 70182544-Bromo-3-methoxyanilineYield 93%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-Bromo-5-nitroanisole (31 g, 134 mmoles) in methanol (700 ml) was added to a mixture of iron powder (22.5 g, 400 mmoles), and ammonium chloride (33.5 g, 630 mmoles) in water (600 ml). The mixture was heated under reflux for 3 hrs. The mixture was allowed to cool and filtered. The filtrate was concentrated in vacuo and the residue partitioned between water and dichloromethane. The organic phase was dried (Na2SO4), filtered and evaporated to dryness to give the title compound (D1) (25 g, 93%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue partitioned between water and dichloromethane
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-320a9075899a4eba8f4fda0d43f4bb45
Source dataset
uspto-grants-1999_07
Patent number
US05922733

Reaction notes

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