Ammonium Chloride → 3-Bromobenzene-1,2-diamine
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
Product 1
Reagents, catalysts & solvents 3
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
- temperatureunder reflux for 1 h
- filtrationfiltered
- extractionextracted with ethyl acetate
- customthe combined organic layers were dried
- concentrationconcentrated in vacuum
Sources & evidence
- ORD record
- ord-506ef317dda5490cb76d82cb879053d9
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388173B2
Reaction notes
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