反应详情

温度

-5 °C

In a 5 liter three neck round bottom flask, 173 g (0.813 mol) of 7-bromo-1,2,3,4-tetrahydroisoquinoline was dissolved carefully into 950 mL of concentrated sulfuric add. The resulting solution was cooled to -5° C. and a solution of 82.7 g (0.816 mol) of potassium nitrate in 1 liter of concentrated sulfuric add was added dropwise. After addition, the reaction was maintained at -5° C. for 15 minutes and poured onto 3 liters of ice. The resulting mixture was basified to pH 14 with 50% sodium hydroxide solution. The basic solution was extracted three times with 1 liter of methylene chloride. The combined organic layers were washed with 1 liter each of water and saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to yield 201 g of an oil. The oil, preadsorbed onto silica gel, was charged onto a column of 4 kg of silica gel and eluted with a gradient of 1-5% methanol/methylene chloride. The fractions containing product were combined and concentrated to yield 115 g of a solid.

1. additionadd
2. additionwas added dropwise
3. additionAfter addition
4. temperaturethe reaction was maintained at -5° C. for 15 minutes
5. extractionThe basic solution was extracted three times with 1 liter of methylene chloride
6. washThe combined organic layers were washed with 1 liter each of water and saturated sodium chloride solution
7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated