Ethyl Acetate → 2-Nitro-3-(trifluoromethyl)aniline
Reaction equation
[N+:1]([C:4]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][C:5]=1[NH:14]C(=O)C)([O-:3])=[O:2].[OH-].[Na+].CCOC(C)=O>CCO>[N+:1]([C:4]1[C:9]([C:10]([F:11])([F:12])[F:13])=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:14])([O-:3])=[O:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 105 °C
Procedure
N-(2-Nitro-3-trifluoromethyl-phenyl)-acetamide (Helvetica 1947, p. 107) (3.6 g) was dissolved in EtOH and heated to 105° C. prior to the addition of 1N NaOH (60 ml) and 50% NaOH (10 ml). After 2.5 h, the reaction was cooled to rt and EtOAc was added. The organic layer was washed with water and brine. Then it was dried and concentrated to give a crude 2-nitro-3-trifluoromethyl-phenylamine (2.79 g): 1H NMR (CDCl3, δppm, 300 mHz) 5.0 (s, 2H), 7.02 (d, 1H), 7.10 (d, 1H), 7.38 (t, 1H).
Workup
- temperaturethe reaction was cooled to rt
- washThe organic layer was washed with water and brine
- customThen it was dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-00ab7e8b0ccc428baa390afaaa795da3
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07696205B2
Reaction notes
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