N-benzyl-7-chloroquinolin-4-amine is obtained by reacting 4,7-dichloroquinoline and aqueous sodium carbonate in microwave radiation.To a solution of 4,7-dichloroquinoline (100 mg, 0.50 mmol) in ethanol (3.00 ml) benzylamine (268 mg, 2.50 mmol) was added and the mixture was reacted at 165 °C for 3 hours under microwave radiation. The resultant mixture was concentrated in vacuo, aqueous sodium carbonate (10ml) was added and this was then extracted with dichloromethane (3×10 ml). The organic extracts collected was dried using magnesium sulphate and concentrated in vacuo to give the title compound as colourless crystals (34 mg, 25%): mp: 175 – 176°C (Lit.: 175 – 178 °C)110;
vmax/cm-1 3320 w (N-H), 2930 w (CH2), 1607 m (C=N), 1576 s and 1448 s (aro. C=C); δH (300 MHz; CDCl3) 8.54, (1H, d, J 5.3, C(2)H), 7.99 (1H, d, J 2.3, C(8)H), 7.70 (1H, d, J 9.0, C(5)H), 7.42-7.38 (5H, m, PhCH), 7.38-7.35 (1H, m, C(6)H), 6.47 (1H, d, J 5.3, C(3)H), 5.31 (1H, s, NH), 4.54 (2H, d, J 5.3, C(10)H2); δC (75 MHz; CDCl3) some signals coincident 152.1 (C(2)H), 149.4 (Ar-C), 149.2 (Ar-C), 137.2 (Ar-C), 135.0 (Ar-C), 129.0 (C(8)H), 129.0 (Ar-CH), 128.0 (Ar-CH), 127.6 (Ar-CH), 125.5 (C(6)H), 120.9 (C(5)H), 117.2 (C), 99.7 (C(3)H), 47.6 (C(10)H2); m/z (+ES) 269 (100%, [M+H]+ with 35Cl), 271 (33%, [M+H]+ with 37Cl); found by +ES 269.0848, C16H14ClN2 ([M+H]+ with 35Cl), requires 269.0841, error 2.8 ppm.
