反应详情

Into a 250 mL 3-necked round bottom flask was added a solution of 5-bromo-2-methyl-8-nitro-1,2,3,4-tetrahydroisoquinoline (4.85 g, 17.89 mmol) in CH3OH/Et3N(anhydrous) (150/15 mL). To the mixture was added Pd/C (4.5 g). Hydrogen gas was bubbled into the mixture The resulting solution was allowed to react, with stirring, for 3 hours while the temperature was maintained at room temperature. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:1). A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was diluted with 50 mL of Na2CO3 (10%). The resulting solution was extracted four times with 50 mL of ethyl acetate and the organic layers combined and dried over Na2SO4. The residue was purified by eluting through a column with a 50:1 CH2Cl2/MeOH solvent system. This resulted in 2.57 g (89%) of 2-methyl-1,2,3,4-tetrahydroisoquinolin-8-amine as a light yellow oil.

1. customHydrogen gas was bubbled into the mixture The resulting solution
2. customto react
3. filtrationA filtration
4. concentrationThe filtrate was concentrated by evaporation under vacuum
5. customa rotary evaporator
6. additionThe resulting solution was diluted with 50 mL of Na2CO3 (10%)
7. extractionThe resulting solution was extracted four times with 50 mL of ethyl acetate
8. dry with materialdried over Na2SO4
9. customThe residue was purified
10. washby eluting through a column with a 50:1 CH2Cl2/MeOH solvent system
11. customThis resulted in 2.57 g (89%) of 2-methyl-1,2,3,4-tetrahydroisoquinolin-8-amine as a light yellow oil