Ethanol → Methyl 2-Amino-4-(trifluoromethyl)benzoate
Reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(O)C>O>[NH2:1][C:4]1[CH:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of methyl 2-nitro-4-(trifluoromethyl)benzoate (2.49 g 0.01 mol), sodium hydrosulfite (8.71 g, 0.05 mol), ethanol (20 ml) and water (20 ml) was heated at 50° C. for 3 h. Water was added and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel with a 5% ethyl acetate/n-hexane to give 1.46 g (6.67 mmol 67%) of the title compound as a white powder.
Workup
- extractionextracted with ethyl acetate
- washThe extracts were washed with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography on silica gel with a 5% ethyl acetate/n-hexane
Sources & evidence
- ORD record
- ord-65a544851a1e4aba8f8f4c560144a16e
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163935B2
Reaction notes
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