Reaktion #2253060

Reaktionsgleichung

1-cyanonaphthalene

dry ice acetone

2,4-dimethylbenzonitrile

potassium

ammonia

ammonia

NH3

→

title compound

Ausbeute 25.1%

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

Ausbeute 25.1%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   Temperaturreflux
3. 3
   workup.ADDITIONcondenser, addition funnel, and a gas inlet
4. 4
   Sonstigegradually evaporated
5. 5
   SonstigeThe crude reaction mixture
6. 6
   SonstigeThe layers were separated
7. 7
   Extraktionthe aqueous phase was extracted with methylene chloride
8. 8
   SonstigeThe combined organic extracts were dried
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe residue was purified by flash chromatography with 2:1 hexane-ethyl acetate
11. 11
    Sonstigethe crude product was recrystallized from 2:1 hexane-ethyl acetate

Vorschrift

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.

Quelle