Ammonium Chloride → Methyl 3-amino-2-bromobenzoate
Reaction equation
[Br:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:12][C:11]1[C:2]([Br:1])=[C:3]([CH:8]=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of methyl 2-bromo-3-nitrobenzoate (4 g, 15.38 mmol) in ethanol (20 mL), ammonium chloride (4 g, 74.07 mmol) dissolved in water (20 mL) and iron powder (6.88 g, 123 mmol) were added under stirring. Resulting reaction mixture was heated at 80° C. for 1 h. On completion, water was added to the mixture and filtered through celite. The filtrate was extracted with ethyl acetate and the combined organic layers washed with water and sodium bicarbonate solution, dried and concentrated under reduced pressure giving the desired methyl 3-amino-2-bromobenzoate (3 g, 85%) which was used without further purification.
Workup
- customResulting
- customreaction mixture
- filtrationfiltered through celite
- extractionThe filtrate was extracted with ethyl acetate
- washthe combined organic layers washed with water and sodium bicarbonate solution
- customdried
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5d8a10dadad34120bb42acded745d7a4
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376422B2
Reaction notes
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