Ammonium Chloride → Chloramben-methyl
Reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:9]([Cl:15])=[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]([Cl:1])=[C:3]([CH:8]=[C:9]([Cl:15])[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 stirred solution of methyl 2,5-dichloro-3-nitrobenzoate (3.3 g, 13.1 mmol) in ethanol (20 mL) was added ammonium chloride (3.5 g, 64.81 mmol) dissolved in water (20 mL) and iron powder (7 g, 82.35 mmol). The reaction mixture was heated at 80° C. for 3 h. On completion, water was added to the reaction mixture and the solids removed by filtration through celite. The filtrate was extracted with ethyl acetate. The combined organic layers were washed with water, dried, and concentrated under reduced pressure to give methyl 3-amino-2,5-dichlorobenzoate (2.5 g, 66%).
Workup
- customthe solids removed by filtration through celite
- 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-893bf9cf8ee6423c82f324a52f6dc42d
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376422B2
Reaction notes
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