| Synthesis | 7-chloro-4-hydrazinoquinoline is prepared byhydrazine monohydrate and 4,7-dichloroquinoline in absolute ethanol.Hydrazine monohydrate (2022 mg, 40.0 mmol) and 4,7-dichloroquinoline (800 mg, 4.00 mmol) were dissolved in absolute ethanol (50 ml). The reaction mixture was left under reflux until the reaction has gone to completion and then allowed to cool in the ice bath for crystallization to occur.
(676 mg, 87%): mp: 220 – 225 ℃ (Lit.: 223 – 225 ℃);
vmax/cm-1 3320 w (N-H), 3050 w (aro. C-H), 1607 m (C=N), 1448 (m, aro. C=C); δH (300 MHz; DMSO-d6) 11.09 (br. s., NH), 8.56-8.40 (2H, m, C(5)H and C(2)H), 7.97 (1H, d, J 1.9, C(8)H), 7.70 (1H, dd, J 9.0, 1.9, C(6)H), 7.10 (1H, d, J 7.2, C(3)H), 5.31 (br. s., NH); δC (75 MHz; DMSO-d6) 155.7 (Ar-C), 142.4 (C(2)H), 138.7 (Ar-C), 137.6 (Ar-C), 126.4 (C(6)H), 125.3 (C(5)H), 119.1 (C(8)H), 113.6 (Ar-C), 98.1 (C(3)H); m/z (-ES) 194 (100%, [M+H]- with 35Cl), 196 (27%, [M+H]- with 37Cl); found by +ES 194.0475, C9H9ClN3 ([M+H]+ with 35Cl), requires 194.0480, error 2.6 ppm. |