Acetic Anhydride → HCID 135858969, compound

Participants

Reaction Conditions

Reaction Steps

Referring to FIG. 19, compound 7 (0.160 g, 0.792 mmol) was added to acetic anhydride (3.5 mL) and the resulting mixture was stirred at 144° C. under nitrogen atmosphere for 7.5 h. Concentrated NaOH solution (50%) was added to the mixture slowly with stirring until the reaction reached pH 12. The solvent was evaporated and the resulting dark brown residue was purified by column chromatography (1:1 EtOAc/hexane) to yield 5b (0.0874 g, 0.475 mmol, 60%) as a yellow solid: 1H NMR (acetone-d6) δ 8.20 (1H, J=8.0 Hz), 8.04 (1H, d, J=8.8 Hz), 7.37 (1H, d, J=8.4 Hz), 7.36 (1H, d, J=9.2 Hz), 2.69 (3H, s); 13C NMR (acetone-d6) δ 163.1, 161.7, 149.1, 136.6, 133.9, 121.0, 117.3, 114.8, 95.7, 24.7; FTIR (neat) 3111, 2922, 2229, 1620, 1577, 1508, 1446, 1342, 1271, 1143, 844 cm−1; MS (ESI) m/z calculated for (C11H8N2O+H)+ 185, found 185; HRMS (ESI) m/z calculated for (C11H8N2O+H)+ 185.0716, found 185.0766.

Provenance & Evidence