Triethylamine → N-(6,7-Methylenedioxyquinolin-4-yl)-N-(N,N-dimethylaminoethyl)-2-bromo-3-nitrobenzamide

Beteiligte Stoffe

Reaktionsschritte

To a solution of compound 7 (259 mg, 1.0 mmol) and triethylamine (0.5 mL) in dry CH2Cl2 (20 mL) was added a solution of 2-bromo-3-nitrobenzoic acid chloride in 20 mL of CH2Cl2 (which was prepared by refluxing of 295 mg, 1.2 mmol of 2-bromo-3-nitrobenzoic acid in 10 mL of thionyl chloride for 4 h). The reaction mixture was heated to reflux for 6 h. The reaction mixture was allowed to cool and then washed with saturated NaHCO3 solution, water and brine and dried over Na2SO4. Solvent was removed in vacuo to give 360 mg of a yellow solid (73.9%); mp 96–97° C.; 1H NMR (CDCl3) δ 2.30 (s, 6H), 2.62 (t, 2H, J=6.6), 3.59–3.69 (m, 1H), 4.53–4.67 (m, 1H), 6.18 (d, 2H, J=5.2), 7.05 (d, 1H, J=7.8), 7.14 (d, 1H, J=7.4) 7.28–7.36 (m, 3H) 7.50 (dd, 1H, J=1.2, 7.8), 8.55 (d, 1H, J=3.8); 13C NMR (CDCl3) δ 45.4, 46.5, 56.4, 97.8, 102.3, 106.7, 112.2, 119.5, 122.6, 125.2, 127.7, 129.7, 140.8, 144.6, 148.3, 148.5, 149.5, 151.4, 166.9

Herkunft & Nachweise