Ammonium Chloride → Methyl 3-Amino-5-bromo-2-methylbenzoate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:13]([O-])=O)[C:5]([CH3:12])=[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]([CH3:12])=[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 a stirred solution of methyl 5-bromo-2-methyl-3-nitrobenzoate (150 g, 544 mmol) in ethanol (750 mL), ammonium chloride (150 g, 2777 mmol) dissolved in water (750 mL) and iron powder (93.3 g, 1636 mmol) were added under stirring. The resulting reaction mixture was heated at 80° C. for 7 h. The reaction mixture was filtered through Celite and the collected solids washed with water and ethyl acetate. The filtrate was extracted with ethyl acetate and the extract dried, concentrated under reduced pressure to give the desired compound methyl 3-amino-5-bromo-2-methylbenzoate which was used as is in further reactions.
Workup
- customThe resulting reaction mixture
- filtrationThe reaction mixture was filtered through Celite
- washthe collected solids washed with water and ethyl acetate
- extractionThe filtrate was extracted with ethyl acetate
- customthe extract dried
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-36a3089c60574e979375553b7de10b0d
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090562B2
Reaction notes
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