3,4,5-Trimethoxybenzoic Acid → 4-(2-Chlorophenyl)-6,8-dimethyl-3-[3-(3,4,5-trimethoxyphenyl)ureido]-quinoline

참여 물질

반응 단계

Triethylamine (0.37 ml) was added dropwise to a mixture of 3,4,5-trimethoxybenzoic acid (563 mg), diphenylphosphoryl azide (730 mg) and dioxane (10 ml) under stirring. The mixture was further stirred for 30 mins. at room temperature and then for 40 mins. under reflux to prepare a solution of 3,4,5-trimethoxyphenyl isocyanate. After cooling, to the resultant solution was added 3-amino-4-(2-chlorophenyl)-6,8-dimethylquinoline (500 mg), and the whole was stirred at room temperature overnight. The reaction mixture was concentrated, and the residue was purified by a column chromatography on silica gel and recrystallized from dichloromethane to give 4-(2-chlorophenyl)-6,8-dimethyl-3-[3-(3,4,5-trimethoxyphenyl)ureido]-quinoline as colorless needles. Yield 490 mg (56.3%). m.p. 204°-206° C.

출처 및 근거