Sulfuric Acid → 2,4,5-Trifluoro-3-methoxyaniline
Reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[C:14]([F:15])=[C:13]([O:16][CH3:17])[C:12]([F:18])=[C:11]([F:19])[C:8]=1C#N.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:17][O:16][C:13]1[C:14]([F:15])=[C:7]([CH:8]=[C:11]([F:19])[C:12]=1[F:18])[NH2:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
50 ml of water and 200 ml of concentrated sulfuric acid were added to 84.4 g (0.42 mole) of 2-amino-4-methoxy-3,5,6-trifluorobenzonitrile (XX) [prepared as described in Step (E2) above]. The mixture was then stirred at 100° C. for 1 hour, after which 150 ml of water were added thereto, and the mixture was stirred at 110°-120° C. for a further 2 hours. The reaction mixture was then allowed to stand to cool to room temperature, after which it was poured into ice-water and neutralized with potassium carbonate. The crystalline substance which precipitated was extracted with ethyl acetate; the extract was washed with water and dried over anhydrous sodium sulfate; and the solvent was removed by evaporation under reduced pressure to afford 57.6 g of 3-methoxy-2,4,5-trifluoroaniline (XXIII) as colorless needles melting at 45°-47° C.
Workup
- stirringthe mixture was stirred at 110°-120° C. for a further 2 hours
- temperatureto cool to room temperature
- customThe crystalline substance which precipitated
- extractionwas extracted with ethyl acetate
- washthe extract was washed with water
- dry with materialdried over anhydrous sodium sulfate
- customand the solvent was removed by evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-d7b7c9bd9f3147648bc300f2aafa4c18
- Source dataset
- uspto-grants-1991_03
- Patent number
- US04997943
Reaction notes
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