反应详情

To a solution of 7-methylquinoline N-oxide (1-2, 246 g, 1.54 mol, 1.0 equiv) in methylene chloride (5 L, 0.31 M) was added TMS-CN (414 ml, 3.1 mol., 2 equiv.) followed by dimethylcarbamoyl chloride (284 ml, 3.1 mol. 2 equiv), and the resulting mixture was stirred at room temperature overnight. The solution was quenched with saturated sodium bicarbonate, diluted with water, and extracted with dichloromethane. The combined organic layers were dried over MgSO4, filtered and the solvent removed to give 260 g of crude material which was recrystallized from methanol to give 186 g of 7-methylquinoline-2-carbonitrile (1-3) in two crops. LRMS m/z (M+H)+ 169.1 found, 169.2 required.

1. customThe solution was quenched with saturated sodium bicarbonate
2. additiondiluted with water
3. extractionextracted with dichloromethane
4. dry with materialThe combined organic layers were dried over MgSO4
5. filtrationfiltered
6. customthe solvent removed
7. customto give 260 g of crude material which
8. customwas recrystallized from methanol