반응 #76499

반응 방정식

product

N-methyl-5-bromo-8-nitrotetrahydroisoquinoline

THF

→

desired product

수율 80.0%

N-(5-bromo-1,2,3,4-tetrahydro-2-methyl-8-isoquinolinyl)acetamide

수율 80.0%

반응 조건

후처리

1. 1
   세척Raney nickel washed with acetone (2×5 mL) and THF (3×5 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   기타the reaction vessel purged with hydrogen
4. 4
   workup.ADDITIONfreshly rinsed catalyst added
5. 5
   workup.WAITAfter 90 minutes
6. 6
   기타The catalyst was removed by filtration
7. 7
   세척washed with THF
8. 8
   기타the filtrate evaporated
9. 9
   workup.DISSOLUTIONThe residue was dissolved in 100 mL acetic anhydride
10. 10
    workup.STIRRINGstirred for 72 hours
11. 11
    기타Excess acetic anhydride was removed in vacuo
12. 12
    세척the solid residue washed with ether
13. 13
    workup.DISSOLUTIONThe solid was dissolved in chloroform
14. 14
    세척washed with saturated sodium bicarbonate
15. 15
    건조The organic layer was dried over magnesium sulfate
16. 16
    여과filtered
17. 17
    기타evaporated
18. 18
    세척The solid was washed with ether
19. 19
    기타dried

실험 절차

A solution of the product of Example 30 (6 g, 22.1 mmol) was dissolved in 100 mL THF. Raney nickel washed with acetone (2×5 mL) and THF (3×5 mL) was added and the reaction vessel purged with hydrogen. The reaction was stirred for 3 hours and freshly rinsed catalyst added. After 90 minutes, the reaction was complete. The catalyst was removed by filtration, washed with THF, and the filtrate evaporated. The residue was dissolved in 100 mL acetic anhydride and stirred for 72 hours. Excess acetic anhydride was removed in vacuo and the solid residue washed with ether. The solid was dissolved in chloroform and washed with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered, and evaporated. The solid was washed with ether and dried to give 5.03 g (80%) of the desired product, mp 192-194° C. (dec).

출처