Water → 4-Bromo-2,6-dimethoxyaniline

HRID 880701Notes

Reaction equation

HRID 880701 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[C:5]([N+:10]([O-])=O)=[C:6]([O:8][CH3:9])[CH:7]=1.O.[Cl-].[NH4+]>CO.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[C:5]([NH2:10])=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 142243345-Bromo-1,3-dimethoxy-2-nitrobenzene

Product 1

HCID 3294234-Bromo-2,6-dimethoxyaniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-1,3-dimethoxy-2-nitro-benzene (2.6 g, 10 mmol) was dissolved in 200 mL of methanol and 40 mL of water was added, followed by 2.5 g of Fe powder and 2.5 g of ammonium chloride. The mixture was heated to reflux at 80° C. for 2 hours and the cooled reaction mixture was filtered and washed with methanol. The filtrate was evaporated under reduce pressure to give the crude product, which was used for next step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. customthe cooled reaction mixture
  3. filtrationwas filtered
  4. washwashed with methanol
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-d6f8c24b10e849fab395758547fb5f8c
Source dataset
uspto-grants-2015_03
Patent number
US08993593B2

Reaction notes

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