Diisopropylethylamine → N-(2,3-dihydro-4-methoxy-3-benzofuranyl)-6-nitro-2-quinolinamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-6-nitro-quinoline (3.8 g, 18.2 mmol) in 1-methyl-2-pyrrolidone (5 mL) with the above described rac-4-methoxy-2,3-dihydro-benzofuran-3-ylamine (3.61 g, 21.9 mmol) and N-ethyldiisopropylamine (4.68 mL, 27.3 mmol) was stirred at 140° C. for 2 h. Cooled to 23° C., poured onto water and extracted twice with ethyl acetate, dried over Na2SO4 and evaporated totally to give a crude product which was purified by silica gel column chromatography with heptane/dichloromethane followed by trituration with diethyl ether to give the title compound as a yellow solid (4.0 g, 65%); MS: m/e=336.3 (M+H+).

Provenance & Evidence