Reaktion #75092

Reaktionsgleichung

3-tert.butyl-1-chloro-4-phenyl isoquinoline

potassium hydroxide

hydrogen

→

3-tert.butyl-4-phenyl isoquinoline hydrochloride

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA mixture of 21.7 g
2. 2
   Sonstigeis hydrogenated at room temperature
3. 3
   FiltrationThe catalyst is filtered off
4. 4
   Waschenwashed with ethanol
5. 5
   Sonstigeare evaporated in vacuo
6. 6
   workup.DISSOLUTIONThe residue is dissolved in ethyl ether
7. 7
   Waschenwashed with water
8. 8
   Sonstigedried
9. 9
   Filtrationfiltered
10. 10
    workup.ADDITIONthe filtrate treated with gaseous HCl
11. 11
    FiltrationThe resulting white solid is filtered
12. 12
    Sonstigerecrystallized from ethanolethyl ether
13. 13
    Waschenwashed with water
14. 14
    Sonstigedried
15. 15
    Filtrationfiltered
16. 16
    workup.ADDITIONthe filtrate treated with gaseous HCl
17. 17
    FiltrationThe resulting white solid is filtered
18. 18
    Sonstigerecrystallized from ethanol-ethyl ether (1:1)

Vorschrift

A mixture of 21.7 g. (0.073 mole) of 3-tert.butyl-1-chloro-4-phenyl isoquinoline, 4.09 g. (0.073 mole) potassium hydroxide, 1.09 g 10% palladium on carbon and 1 liter of ethanol is hydrogenated at room temperature and 50 psi until 1 equivalent of hydrogen is absorbed. The catalyst is filtered off and washed with ethanol, combined ethanol portions are evaporated in vacuo. The residue is dissolved in ethyl ether, washed with water, dried, and filtered and the filtrate treated with gaseous HCl. The resulting white solid is filtered and recrystallized from ethanolethyl ether, washed with water, dried, and filtered and the filtrate treated with gaseous HCl. The resulting white solid is filtered and recrystallized from ethanol-ethyl ether (1:1) to give 3-tert.butyl-4-phenyl isoquinoline hydrochloride; m.p. 236°-238° C.

Quelle