Synthesis
General procedure for the synthesis of quinoline-4-carbonitrile from 4-quinolinecarboxaldehyde: 4-quinolinecarboxaldehyde (54 mg, 0.5 mmol) and ammonium acetate (385 mg, 5.0 mmol) were dissolved in acetonitrile (6 mL) at room temperature, followed by the addition of trimethylphenyltrimethylammonium (376 mg, 1.0 mmol). The reaction mixture was stirred continuously for 21 hours at room temperature. Upon completion of the reaction, the reaction mixture was sequentially treated with 0.5 M Na2S2O3 aqueous solution (10 mL) and 1.0 M NaHCO3 aqueous solution (15 mL) and then extracted with ethyl acetate (60 mL). The organic phase was washed sequentially with 0.5 M Na2S2O3 aqueous solution and saturated NaCl aqueous solution and finally dried with anhydrous MgSO4.
References
[1] Heterocycles, 2016, vol. 92, # 10, p. 1796 - 1802
[2] Patent: EP1555257, 2005, A1. Location in patent: Page/Page column 24
