반응 #2253060

반응 방정식

1-cyanonaphthalene

dry ice acetone

2,4-dimethylbenzonitrile

potassium

ammonia

ammonia

NH3

→

title compound

수율 25.1%

6-Methyl-3-(1-naphthalenyl)-1-isoquinolineamine

수율 25.1%

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
   기타The layers were separated
7. 7
   추출the aqueous phase was extracted with methylene chloride
8. 8
   기타The combined organic extracts were dried
9. 9
   농축concentrated
10. 10
    기타The residue was purified by flash chromatography with 2:1 hexane-ethyl acetate
11. 11
    기타the crude product was recrystallized from 2:1 hexane-ethyl acetate

실험 절차

A 250-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 (175 mL). Iron (III) nitrate nonahydrate (0.23 g, 0.57 mmol) was added to the liquid NH3 in one portion as a solid, and then potassium metal (4.2 g, 107.4 mmol) was added cautiously in small portions. A solution of 2,4-dimethylbenzonitrile (7.0 g, 53.4 mmol) in THF (20 mL) was added to the reaction mixture dropwise over a period of 5 minutes, the reaction was stirred for 15 minutes, a solution of 1-cyanonaphthalene (12.6 g, 79.8 mmol) in THF (30 mL) was then added dropwise over a period of 10 minutes, and the reaction mixture was allowed to stir overnight as the liquid ammonia gradually evaporated. The crude reaction mixture was cautiously poured into excess ice water. The layers were separated, 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 (3.82 g, 13.4 mmol, 24% yield) as a solid: mp 170°; IR(CHCl3) 3512, 3409 cm-1 ; MS m/e 285(M+ +H); 1H NMR(CDCl3) δ 8.13-8.23(m,1H), 7.80-7.97(m,2H), 7.62-7.78(m,2H), 7.37-7.61(m,1H), 7.27-7.36(m,1H), 7.17-7.26(m,1H), 5.28(s,2H), 2.51(s,3H); HRMS m/e calcd for C20H16N2 (M+) 284.1315, Found 284.1305. Anal. Calcd for C20H16N2 : C,84.48; H,5.67; N,9.85. Found: C,84.39; H,5.63; N,9.57.

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