4-Quinolinecarboxaldehyde → HCID 54080304, compound

Participants

Reaction Steps

Quinolin-4-carboxaldehyde (4.71 g; 0.03 mol) and 3-pyridylacetonitrile (3.54 g; 0.03 mol) were dissolved in ethanol (100 mL). Sodium methoxide (2 mL of 25% methanol solution) was added. The reaction mixture was heated at reflux for a period of 2.5 hours. The mixture was cooled to ambient temperature. After 18 hours, the precipitated solid was collected, suspended in ethanol and saturated with hydrogen chloride gas. The mixture was cooled and the solid was collected by filtration. The solid was crystallized from methanol to give the title compound (5.8 g; 57% yield) as a dihydrochloride, three quarter hydrate, yellow solid, m.p. 250° C. (dec.). Anal. Calcd for C17H11N3 ·HCl·3/4 H2O; C, 59.40; H, 4.25; N, 12.23. Found: C, 59.75; H, 4.10; N, 11.93. Mass spectrum (EI; M+) m/z 257. 1 H-NMR (DMSO-d6 ; 400 MHz) δ 9.40 (s, 1H), 9.38 (d, 1H), 9.15 (s, 1H), 8.93 (d, 1H), 8.74 (d, 1H), 8.56 (d, 1H), 8.46 (d, 1H), 8.32 (d, 1H), 8.13 (t, 1H), 8.00 (q, 1H), 7.95 (t, 1H), and 7.70 ppm (br s, 4H).

Provenance & Evidence