8-Nitroquinoline

91-22-5

607-35-2

607-34-1

General procedure for the synthesis of 8-nitroquinoline and 5-nitroquinoline from quinoline: Pure sulfuric acid (H2SO4) was slowly added to 1 equivalent of quinoline at 0 °C. Subsequently, 3 equivalents of 65% nitric acid (HNO3) were added dropwise and the reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the mixture was poured sequentially into water, neutralized with sodium carbonate (Na2CO3) and then extracted twice with dichloromethane. The organic layer was washed with water and dried with anhydrous sodium sulfate (Na2SO4) followed by evaporation of the solvent under vacuum. 8-Nitroquinoline (compound 35) was obtained as a light yellow solid in 34% yield; melting point 90 °C, literature value: 89-90 °C [43].1H NMR (200 MHz, CDCl3) δ: 7.53-7.66 (m, 2H), 8.04 (d, J=8.0 Hz, 2H), 8.27 (dd, J=1.6 and 8.4 Hz, 1H). 9.70 (dd, J=1.7 and 4.2 Hz, 1H). 13C NMR (50 MHz, CDCl3) δ: 122.8 (CH), 123.8 (CH), 125.3 (CH), 129.0 (C), 132.0 (CH), 136.1 (CH), 139.5 (C), 148.2 (C), 152.6 (CH ). Recrystallization by isopropanol afforded 5-nitroquinoline (compound 36) as a light yellow solid in 38% yield; melting point 71 °C, literature value: 71-72 °C [41].1H NMR (200 MHz, CDCl3) δ: 7.61-7.68 (m, 1H), 7.76-7.85 (m, 1H), 8.36-8.45 (m, 2H). 8.98-9.04 (m, 2H).13C NMR (50MHz, CDCl3) δ: 121.2 (C), 123.9 (CH), 124.6 (CH), 127.5 (CH), 131.9 (CH), 136.6 (CH), 145.5 (C), 148.2 (C), 151.6 (C).