Hydrochloric Acid → HCID 53723184, compound

Temperature

-60 °C

4-Chloro-3-methoxy-6-trifluoromethylanthranilic acid (5 mg, 0.019 mmol) was dissolved in diethyl ether (1 mL) and HCl (2M, 20 L) was added. The solution was evaporated and co-evaporated with toluene. The residue was dissolved in CH2Cl2 (2 mL), cooled to -60° C., and BBr3 (9 L, 0.092 mmol) was added followed by stirring at -60° C. for 3 min, 0° C. for 3 h and room temperature for 6 h. Additional BBr3 (4 L, 0.04 mmol) was added at -35° C. and the stirring was continued at room temperature for 2 h. The reaction mixture was cooled to -20 ° C. and added to ice-cold NaHCO3 (2 mL, sat.) followed by stirring for 1 h at room temperature. Methylene chloride (2 mL) was added and pH was adjusted to 5. The phases were separated and the H2O phase was washed with EtOAc (3). The combined organic layers were dried (Na2SO4), filtered and evaporated. The crude product was purified on a silica gel coloumn (EtOAc EtOAc-HOAc 100:1) and the title compound was isolated (3 mg). 1H NMR (CD3OD): 6.97 (s, 1 H). MS (EI, 70 eV): m/z (rel. int.) 257/255 (M+, 0.16/0.54)

1. customThe solution was evaporated
2. dissolutionThe residue was dissolved in CH2Cl2 (2 mL)
3. waitthe stirring was continued at room temperature for 2 h
4. temperatureThe reaction mixture was cooled to -20 ° C.
5. stirringby stirring for 1 h at room temperature
6. customThe phases were separated
7. washthe H2O phase was washed with EtOAc (3)
8. dry with materialThe combined organic layers were dried (Na2SO4)
9. filtrationfiltered
10. customevaporated
11. customThe crude product was purified on a silica gel coloumn (EtOAc EtOAc-HOAc 100:1)

ORD record

ord-0046e74470a448b69d9225c9accee376

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05883129