反应详情

温度

0 °C

Into a 50 mL 3-necked round bottom flask (named A), was placed 2-methyl-1,2,3,4-tetrahydroisoquinolin-8-amine (500 mg, 3.08 mmol). This was followed by the addition of a solution of HBr (5 mL) in H2O (5 mL), which was added dropwise with stirring, while cooling to a temperature of 0° C. To the above was added NaNO2 (230 mg, 3.33 mmol) in several batches, while cooling to a temperature of 0° C. and the mixture was stirred for 30 mins at that temperature. Then into another 50 mL 3-necked round bottom flask (named B), was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of CuBr (550 mg, 3.83 mmol) in HBr/H2O (3 mol/L) (10 mL), while cooling to a temperature of 0° C. The mixture was stirred for 10 minutes. Then was followed by the addition of the reaction solution of flask A with dropwise while the temperature was maintained at 0° C. The resulting solution was allowed to react, with stirring, for 30 minutes while the temperature was maintained at 0° C. The resulting solution was allowed to react, with stirring, for an additional 2 hours at room temperature. The reaction progress was monitored by TLC(ethyl acetate:petroleum ether=1:1). Adjustment of the pH to 9 was accomplished by the addition of NaOH (10%). The resulting solution was extracted three times with 50 mL of CH2Cl2 and the organic layers combined and dried over K2CO3. A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluting through a column with a 1:1 ethyl acetate; petroleum ether solvent system. This resulted in 0.45 g (65%) of 8-bromo-2-methyl-1,2,3,4-tetrahydroisoquinoline as light yellow oil.

1. customInto a 50 mL 3-necked round bottom flask (named
2. additionwas added dropwise
3. temperaturewhile cooling to a temperature of 0° C.
4. stirringthe mixture was stirred for 30 mins at that temperature
5. customThen into another 50 mL 3-necked round bottom flask (named B), was purged
6. temperaturemaintained with an inert atmosphere of nitrogen
7. temperaturewhile cooling to a temperature of 0° C
8. stirringThe mixture was stirred for 10 minutes
9. additionThen was followed by the addition of the reaction solution of flask A with dropwise while the temperature
10. temperaturewas maintained at 0° C
11. customto react
12. stirringwith stirring, for 30 minutes while the temperature
13. temperaturewas maintained at 0° C
14. customto react
15. stirringwith stirring, for an additional 2 hours at room temperature
16. extractionThe resulting solution was extracted three times with 50 mL of CH2Cl2
17. dry with materialdried over K2CO3
18. filtrationA filtration
19. concentrationThe filtrate was concentrated by evaporation under vacuum
20. customa rotary evaporator
21. customThe residue was purified
22. washby eluting through a column with a 1:1 ethyl acetate
23. customThis resulted in 0.45 g (65%) of 8-bromo-2-methyl-1,2,3,4-tetrahydroisoquinoline as light yellow oil