Triethylamine → N-(6,7-Methylenedioxyquinolin-4-yl)-N-(N,N-dimethylaminoethyl)-2-bromo-5-nitrobenzamide

Participants

Reaction Steps

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-5-nitrobenzoic acid chloride in 20 mL of CH2Cl2 (which was prepared by refluxing of 295 mg, 1.2 mmol of 2-bromo-5-nitrobenzoic acid in 10 mL of thionyl chloride for 3 h.) and reaction mixture was heated to reflux for 4 h. The reaction mixture was washed with saturated NaHCO3 solution, water and brine and dried over Na2SO4. The solvent was removed in vacuo to give a yellow solid; yield 350 mg (71.8%); mp 204–5° C.; 1H NMR (CDCl3) δ (2.3, s, 6H), 2.53–2.64 (m, 2H), 3.67–3.81 (m, 1H), 4.42–4.55 (m, 1H), 6.19 (s, 2H), 7.31 (s, 1H), 7.34 (d, 1H, J=4.8), 7.43 (s, 1H), 7.52 (d, 1H, J=8.8), 7.76 (dd, 1H, J=2.6, 8.4), 7.87 (d, 1H, J=2.6), 8.53 (d, 1H, J=4.8); 13C NMR (CDCl3) δ 45.4, 46.6, 56.4, 97.9, 102.4, 106.6, 119.4, 122.3, 122.8, 124.6, 127.2, 134.0, 139.0, 144.5, 145.9, 148.1, 148.5, 149.6, 151.5, 166.5.

Provenance & Evidence