반응 #2253061

반응 방정식

5-chloro-2-methylbenzonitrile

dry ice acetone

1-cyanonaphthalene

potassium

ammonia

NH4Cl

ammonia

→

title compound

수율 14.3%

7-Chloro-3-(1-naphthalenyl)-1-isoquinolineamine

수율 14.3%

용매

THF

THF

반응 조건

후처리

1. 1
   온도cooled
2. 2
   온도reflux
3. 3
   workup.ADDITIONcondenser, addition funnel, and a gas inlet
4. 4
   기타gradually evaporated
5. 5
   기타The crude reaction mixture
6. 6
   추출the aqueous phase was extracted with methylene chloride
7. 7
   기타The combined organic extracts were dried
8. 8
   농축concentrated
9. 9
   기타The residue was purified by flash chromatography with 2:1 hexane-ethyl acetate
10. 10
    기타the crude product was recrystallized from 2:1 hexane-ethyl acetate

실험 절차

A 500-mL, three-necked, round-bottomed flask equipped with a dry ice-acetone cooled reflux condenser, addition funnel, and a gas inlet was charged with liquid ammonia (150 mL). Iron (III) nitrate nonahydrate (spatula end) was added in one portion as a solid, and then potassium metal (5.16 g, 132.0 mmol) was added cautiously in small portions. A solution of 5-chloro-2-methylbenzonitrile (10.00 g, 65.96 mmol) in THF (30 mL) was added dropwise over 5 minutes, the reaction mixture was stirred for 5 minutes, a solution of 1-cyanonaphthalene (15.16 g, 98.97 mmol) in THF was added dropwise over 5 minutes, and the reaction mixture was allowed to stir overnight as the liquid ammonia gradually evaporated. The crude reaction mixture was cautiously poured into saturated aqueous NH4Cl, and the aqueous phase was extracted with methylene chloride. The combined organic extracts were dried and concentrated. The residue was purified by flash chromatography with 2:1 hexane-ethyl acetate, and the crude product was recrystallized from 2:1 hexane-ethyl acetate to afford the title compound (2.88 g, 9.45 mmol, 14% yield) as yellow crystals: mp 180°-181°; IR(CHCl3) 3513, 3409 cm-1 ; MS m/e 305 (M+ +H NMR(CDCl3) δ 8.00-8.17(m,1H), 7.83-8.00(m,2H), 7.80(s,1H), 7.33-7.79(m,6H), 7.25(s,1H), 5.35(s,2H). Anal. Calcd for C19H13ClN2 : C,74.88; H,4.30; Cl,11.83; N,9.19. Found: C,74.77; H,4.09; Cl,11.87; N,8.81.

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