Reaktion #318733

Reaktionsgleichung

charcoal

Sodium hydride

1-cyano-2-benzenesulfonyl-1,2-dihydro-5-methoxyisoquinoline

→

cyanoisoquinoline

1 -Cyano-5-methoxyisoquinoline

Lösungsmittel

xylene

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is refluxed under nitrogen for 3 hrs
2. 2
   Filtrationfiltered
3. 3
   WaschenThe filtered solid is washed with xylenes
4. 4
   SonstigeThe filtrate is evaporated in vacuo
5. 5
   workup.STIRRINGThe filtered solid is stirred with methylene chloride and aqeuous 5% sodium hydroxide solution
6. 6
   Waschenthe combined extracts are washed with 5% sodium hydroxide solution, H2O
7. 7
   Trocknendried over sodium sulfate
8. 8
   ExtraktionThe dried extract
9. 9
   Filtrationis filtered
10. 10
    Sonstigethe filtrate evaporated in vacuo
11. 11
    Sonstigeaffording a moist solid which
12. 12
    Sonstigeis triturated in hexanes
13. 13
    FiltrationThe triturated solid is filtered
14. 14
    Waschenwashed with hexanes
15. 15
    Sonstigedried
16. 16
    Sonstigeaffording a fluffy orange solid, M.P. 166°-175° C
17. 17
    Filtrationfiltered
18. 18
    Sonstigerecrystallized from ethyl acetate

Vorschrift

Sodium hydride (1.2 g of 60% in mineral oil) is added to a stirred suspension of 1-cyano-2-benzenesulfonyl-1,2-dihydro-5-methoxyisoquinoline (10 g) in xylene (100 ml). The reaction mixture is refluxed under nitrogen for 3 hrs, cooled to RT, stirred for an additional hour, and filtered. The filtered solid is washed with xylenes. The filtrate is evaporated in vacuo. The filtered solid is stirred with methylene chloride and aqeuous 5% sodium hydroxide solution. The methylene chloride phase is combined with the residue from the evaporated filtrate and the combined extracts are washed with 5% sodium hydroxide solution, H2O and dried over sodium sulfate. The dried extract is filtered and the filtrate evaporated in vacuo, affording a moist solid which is triturated in hexanes. The triturated solid is filtered, washed with hexanes, and dried, affording a fluffy orange solid, M.P. 166°-175° C. The crude product is dissolved in ethyl acetate, treated with charcoal, filtered and recrystallized from ethyl acetate, affording the desired cyanoisoquinoline as a crystalline solid, M.P. 180°-182° C.

Quelle