Acrylic Acid → 3-(3-Trifluoromethylphenylamino)propionic acid

Temperature

100 °C

Water (150 mL) and acrylic acid (48 g) were added to 3-aminobenzotrifluoride (75 g). The reaction mixture was stirred at 100° C. for one hour. The solution was cooled to room temperature. The pH of the solution was then adjusted to 10 with a 1 N aqueous sodium hydroxide solution. The solution was washed with diethyl ether, and the pH of the solution was then adjusted to 3 with 1 N hydrochloric acid. The solution was extracted with diethyl ether. The organic layer was washed with a saturated brine and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate=2:1). The title compound (82 g) was obtained as a white solid.

1. temperatureThe solution was cooled to room temperature
2. washThe solution was washed with diethyl ether
3. extractionThe solution was extracted with diethyl ether
4. washThe organic layer was washed with a saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. distillationThe solvent was distilled off under reduced pressure
7. customThe residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate=2:1)

ORD record

ord-d0a6208ff7b3436786d77e6f49b4901c

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07910751B2