8-Hydroxyquinoline-5-carbaldehyde → HCID 135744156, compound

Participants

Reaction Steps

Amine 4 (0.726 g, 0.00376 mol) and 5-formyl-8-hydroxyquinoline 6 (0.650 g, 0.00376 mol) were dissolved in 40 mL of benzene and refluxed for 18 hours. After cooling, the solvent was removed under reduced pressure to yield the product as an orange solid (1.308 g, 100%). 1H NMR (300 MHz, CDCl3) δ9.75 (1H, dd J=8.79, 1.64); 8.81 (1H, dd, J=1.64, 4.39); 8.59 (1H, s); 7.69 (1H, d, J=8.24); 7.56 (1H, dd, J=4.39, 8.79); 7.19 (1H, d, J=7.69); 6.10 (1H endo, dd, J=2.74, 5.49); 6.06–5.99 (2H exo, m); 5.91 (1H endo, dd, J=2.74, 5.94); 3.67 (2H, t, J=7.14); 2.74 (2H, s); 1.99–1.69 (4H, m); 1.42–1.01 (12H, m); 0.50–0.44 (1H, m). 13C NMR (75 MHz, CDCl3) δ160.8; 154.2; 148.1; 138.4; 137.0; 135.3; 133.0; 132.6; 127.0; 123.3; 123.2; 109.2; 62.9; 49.7; 45.6; 42.7; 38.9; 34.9; 32.6; 31.4; 29.9; 28.8; 27.6. HRMS (EI): calcd for C23H28N2O1 [M]+348.2201, found 348.2186.

Provenance & Evidence