Ammonium Chloride → HCID 63022790, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:13]([O-])=O)[C:5]([Cl:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:13][C:4]1[C:5]([Cl:12])=[C:6]([CH:11]=[C:2]([Br:1])[CH:3]=1)[C:7]([O:9][CH3:10])=[O:8]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
To stirred solution of methyl 5-bromo-2-chloro-3-nitrobenzoate (3.4 g, 11.6 mmol) in ethanol (19 mL) was added ammonium chloride (3.4 g, 57.8 mmol) dissolved in water (30 mL) and iron powder (5.16 g, 92.5 mmol). The reaction mixture was heated at 80° C. for 1 h. On completion, the reaction mixture was filtered through celite washing with ethanol and ethylacetate. The filtrate was extracted with ethyl acetate and the combined organic layers were washed with water, dried and concentrated under reduced pressure to give methyl 3-amino-5-bromo-2-chlorobenzoate (2.8 g, 92.1%).
Workup
- filtrationOn completion, the reaction mixture was filtered
- washthrough celite washing with ethanol and ethylacetate
- extractionThe filtrate was extracted with ethyl acetate
- washthe combined organic layers were washed with water
- customdried
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-8b1840ddb1254fb5b94dbbad3d749db4
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376422B2
Reaction notes
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