Hydrochloric Acid → HCID 68663801, compound

Temperature

80 °C

To a solution of 2-chloro-5-(trifluoromethyl)aniline (2.15 g, 11.00 mmol) in diethylene glycol dimethyl ether (20 mL) was added sodium hydride (60% in oil, 440 mg, 11.00 mmol), and the resulting mixture was stirred at 80° C. for 30 min. To this reaction mixture was added methyl 3-fluoro-4-nitrobenzoate (1.99 g, 10.00 mmol), and the resulting mixture was stirred at 80° C. for 1 hr. After cooling, 1 M hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1M hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=20/1) and recrystallized from hexane/ethyl acetate to give crude methyl 3-[[2-chloro-5-(trifluoromethyl)phenyl]amino]-4-nitrobenzoate (1.92 g).

1. stirringthe resulting mixture was stirred at 80° C. for 1 hr
2. temperatureAfter cooling
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with 1M hydrochloric acid and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=20/1)
8. customrecrystallized from hexane/ethyl acetate

ORD record

ord-560f80c7e4ac4c998442ea452dfc47e4

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08492378B2