Acetic Acid → HCID 54120139, compound

Participants

Reaction Steps

6-Chloro-7-methoxy-4-trifluoromethylisatin (13 mg, 0.046 mmol) was dissolved in NaOH (0.68M, 0.20 mL, 0.13 mmol) and H2O (0.20 mL) and then cooled to +7 C. Hydrogen peroxide (30%, 14 L, 0.14 mmol) dissolved in NaOH (0.68M, 0.49 mL, 0.33 mmol) was added dropwise during 1 min. The reaction mixture was stirred for 1 h 15 min at room temperature. Additional H2O2 (10 L) was added at 7 C. and then stirring was continued at room temperature for 2 h. Acetic acid (54 L, 0.94 mmol) was added, but no precipitation occured. Ethyl acetate (2 mL) was added and pH was raised to 6 with NaHCO3 (aq, sat.). The water phase was washed with EtOAc (3) and the combined organic layers were evaporated and co-evaporated with toluene (2). Purification by flash chromatography (SiO2, gradient EtOAc EtOAc-HOAc 100:1) yielded the title compound (5 mg). 1H NMR (CD3OD): 6.98 (s, 1H), 3.87 (s, 3H). MS (EI, 70 eV): m/z (rel. int.) 271/269 (M+, 17/48).

Provenance & Evidence