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
Preparation I5, Step 1: 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, δ ppm, 300 mHz) 5.0 (s, 2H), 7.02 (d, 1H), 7.10 (d, 1H), 7.38 (t, 1H).
Workup
- customPreparation I5, Step 1
- 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-65e4e256c73a4ece9a5407570b7e1c57
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07378409B2
Reaction notes
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