Ammonium Chloride → 3-Bromobenzene-1,2-diamine

HRID 1051513Notes

Reaction equation

HRID 1051513 reaction equation
[Br:1][C:2]1[C:3]([N+:9]([O-])=O)=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[NH4+].[Cl-]>CCO.O.[Fe]>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:4]([NH2:5])[C:3]=1[NH2:9]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 218520723-Bromo-2-nitroaniline

Product 1

HCID 124898393-Bromobenzene-1,2-diamineYield 98.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-bromo-2-nitroaniline (2 g, 9.2 mmol), Fe powder (1.54 g, 27.6 mmol) and NH4Cl (4.8 g, 52 mmol) in EtOH and H2O was stirred under reflux for 1 h. The mixture was cooled to room temperature and filtered. The filtrate was diluted water extracted with ethyl acetate and the combined organic layers were dried and concentrated in vacuum to give the crude desired product (1.7 g, Yield 85%). This crude was used in the next step without further purification.

Workup

  1. temperatureunder reflux for 1 h
  2. filtrationfiltered
  3. extractionextracted with ethyl acetate
  4. customthe combined organic layers were dried
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-506ef317dda5490cb76d82cb879053d9
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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