반응 #2016047

반응 방정식

2-chloro-6-nitro-quinoline

rac-4-(2-methoxy-ethoxy)-2,3-dihydro-benzofuran-3-ylamine

N-ethyldiisopropylamine

→

title compound

수율 65.0%

rac-[4-(2-Methoxy-ethoxy)-2,3-dihydro-benzofuran-3-yl]-(6-nitro-quinolin-2-yl)-amine

수율 65.0%

용매

1-methyl-2-pyrrolidone

반응 조건

후처리

1. 1
   온도Cooled to 23° C.
2. 2
   workup.ADDITIONpoured onto water
3. 3
   추출extracted twice with ethyl acetate
4. 4
   건조dried over Na2SO4
5. 5
   기타evaporated totally
6. 6
   기타to give a crude product which
7. 7
   기타was purified by silica gel column chromatography with heptane/dichloromethane

실험 절차

A mixture of 2-chloro-6-nitro-quinoline (1.04 g, 5.0 mmol) in 1-methyl-2-pyrrolidone (10 mL) with the above described rac-4-(2-methoxy-ethoxy)-2,3-dihydro-benzofuran-3-ylamine (1.14 g, 5.5 mmol) and N-ethyldiisopropylamine (1.27 mL, 7.5 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 an orange solid (1.24 g, 65%); MS: m/e=382.3 (M+H−).

출처