反应详情

4,5-Dimethoxy-2-nitroaniline and 3-penten-2-one were subjected to a Skraup reaction. A black, tarry substance was obtained, from which an orange solid could be isolated by chromatography over silica gel using benzene-ethyl acetate (19:1) to elute the product. That material was thrice crystallized from 2-propanol, re-chromatographed, and again crystallized to afford 14% yield of golden 5,6-dimethoxy-2,4-dimethyl-8-nitroquinoline. Although it melted 85°-108°, it showed a single spot on two tlc systems.

1. customA black, tarry substance was obtained, from which an orange solid
2. customcould be isolated by chromatography over silica gel
3. washto elute the product
4. customcrystallized from 2-propanol
5. customre-chromatographed
6. customagain crystallized