反应详情

A mixture of 4-bromo-5,8-dimethyl-6-nitroquinoline (3.87 g, 13.77 mmol), cuprous cyanide (3.67 g, 41.31 mmol) and dimethylformamide (70 mL) is stirred at room temperature for 30 minutes and then heated to 155° C. and stirred at this temperature for 1 hour. Water is added, and the reaction mixture is filtered. The precipitate is washed with water and methylene chloride. The filtrate is extracted with methylene chloride (3×125 mL), and the combined organic layers are dried (sodium sulfate) and evaporated. Purification by chromatography through a short column consisting of layers of sand/flash silica gel/sand, using chloroform as eluent, provides 4-cyano-5,8-dimethyl-6-nitroquinoline.

1. temperatureheated to 155° C.
2. stirringstirred at this temperature for 1 hour
3. filtrationthe reaction mixture is filtered
4. washThe precipitate is washed with water and methylene chloride
5. extractionThe filtrate is extracted with methylene chloride (3×125 mL)
6. dry with materialthe combined organic layers are dried (sodium sulfate)
7. customevaporated
8. customPurification by chromatography through a short column