反应详情

温度

78 °C

2-chloro-8-nitroquinoline (0.20 g; 0.96 mmol) is suspended in 9.5 ml of 1-butylamine and the medium is heated under reflux (78° C.) for 15 hours. The yellow solution obtained is subsequently concentrated under vacuum. The crude reaction product is taken up in a minimum volume of CH3OH and poured over 3 ml of diethyl ether. After centrifugation, butyl ammonium chloride crystals are removed and the supernatant is concentrated under reduced pressure to yield N-butyl-8-nitro-2-quinoline amine in the form of a yellow oil (0.21 g; 0.86 mmol, yield=90%). NMR-1H (250 MHz, CDCl3) δ, ppm: 7.83 (dd, 3J (H, H)=7.5 Hz, 4J (H, H)=1.5 Hz, 1H); 7.77 (d, 3J (H, H)=9.0 Hz, 1H); 7.69 (dd, 3J (H, H)=8.0 Hz, 4J (H, H)=1.5 Hz, 1H); 7.14 (m, 1H), 6.67 (d, 3J (H, H)=9.0 Hz, 1H); 5.07 (s large, 1H); 3.47 (m, 2H); 1.60 (m, 2H); 1.39 (m, 2H); 0.93 (t, 3J (H, H)=7.5 Hz, 3H). NMR-13C (63 MHz, CDCl3) δ, ppm: 157.8 (Cq); 145.6 (Cq); 140.2 (Cq); 136.7 (CH); 131.5 (CH); 124.7 (CH); 124.1 (CH); 119.7 (CH); 113.3 (Cq); 41.3 (CH2); 31.5 (CH2); 20.2 (CH2); 13.8 (CH3). MS (CID, NH3): m/z=246 (MH+). Analysis (%) for C13H15N3O2: calculated C, 63.66. H, 6.16. N, 17.13. found C, 63.33. H, 6.21. N, 16.64.

1. temperaturethe medium is heated
2. customThe yellow solution obtained
3. concentrationis subsequently concentrated under vacuum
4. customThe crude reaction product
5. customAfter centrifugation, butyl ammonium chloride crystals are removed
6. concentrationthe supernatant is concentrated under reduced pressure