Hydrochloric Acid → HCID 53723184, compound

Participants

Reaction Conditions

Reaction Steps

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)

Provenance & Evidence