Ammonium Chloride → 3-Amino-2-methylbenzoic acid methyl ester
Reaction equation
[CH3:1][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]([CH3:1])=[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-methyl-3-nitrobenzoate (10.0 g, 56.4 mmol) in 60 ml of ethanol were added ammonium chloride (18.0 g, 338 mmol) dissolved in 60 mL of water and iron powder (18.8 g, 338.2 mmol). The resulting reaction mixture was heated at 80° C. for 3 h. Water was added to the reaction mixture and then it was filtered through celite. The filtrate was extracted with ethyl acetate. The combined organic layers were washed with water, dried over Na2SO4, concentrated under reduced pressure to give the title compound (7.0 g, 83%).
Workup
- customThe resulting reaction mixture
- filtrationit was filtered through celite
- extractionThe filtrate was extracted with ethyl acetate
- washThe combined organic layers were washed with water
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-95fd3c26c8d94ff89d42c5004f204797
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376422B2
Reaction notes
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