Reaktion #76499

Reaktionsgleichung

product

N-methyl-5-bromo-8-nitrotetrahydroisoquinoline

THF

→

desired product

Ausbeute 80.0%

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

Ausbeute 80.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenRaney nickel washed with acetone (2×5 mL) and THF (3×5 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   Sonstigethe reaction vessel purged with hydrogen
4. 4
   workup.ADDITIONfreshly rinsed catalyst added
5. 5
   workup.WAITAfter 90 minutes
6. 6
   SonstigeThe catalyst was removed by filtration
7. 7
   Waschenwashed with THF
8. 8
   Sonstigethe filtrate evaporated
9. 9
   workup.DISSOLUTIONThe residue was dissolved in 100 mL acetic anhydride
10. 10
    workup.STIRRINGstirred for 72 hours
11. 11
    SonstigeExcess acetic anhydride was removed in vacuo
12. 12
    Waschenthe solid residue washed with ether
13. 13
    workup.DISSOLUTIONThe solid was dissolved in chloroform
14. 14
    Waschenwashed with saturated sodium bicarbonate
15. 15
    TrocknenThe organic layer was dried over magnesium sulfate
16. 16
    Filtrationfiltered
17. 17
    Sonstigeevaporated
18. 18
    WaschenThe solid was washed with ether
19. 19
    Sonstigedried

Vorschrift

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).

Quelle