Ethanol → Methyl 3-amino-2-bromobenzoate
Reaction equation
[Br:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].[Cl-].[NH4+].[CH2:16](O)C>O.[Fe]>[NH2:11][C:10]1[C:2]([Br:1])=[C:3]([CH:7]=[CH:8][CH:9]=1)[C:4]([O:6][CH3:16])=[O:5]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To stirred solution of above crude 2-bromo-3-nitrobenzoate (4 g, 15.38 mmol) in ethanol (20 mL), ammonium chloride (4 g, 74.0 mmol) dissolved in water (20 mL) and iron powder (6.87 g, 123 mmol) were added under stirring. The resulting reaction mixture was heated at 80° C. for 7 h. On completion, the reaction mixture was filtered through celite, washing with water and ethyl acetate and the filtrate extracted with ethyl acetate. The combined organic layers were dried and concentrated under reduced pressure giving the desired crude product (3 g).
Workup
- customThe resulting reaction mixture
- filtrationOn completion, the reaction mixture was filtered through celite
- washwashing with water and ethyl acetate
- extractionthe filtrate extracted with ethyl acetate
- customThe combined organic layers were dried
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b6491b6b80aa4f58a3fcb7aa17b2fe9c
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376422B2
Reaction notes
Loading…