Synthesis
A mixed solution of nitric acid (16 mL) and sulfuric acid (8 mL) was slowly added dropwise to a solution of sulfuric acid (150 mL) containing 2-chloroquinoline (61.1 mmol) at 20 °C, keeping the reaction temperature at 0 °C. Subsequently, the reaction mixture was warmed up to 40 °C and maintained for 30 min. Upon completion of the reaction, the reaction was quenched with ice water (800 mL). The precipitated solid product was collected by filtration and purified by fast chromatography (eluent ratio of 20:1 petroleum ether/ethyl acetate) to finally obtain the target compound 2-chloro-8-nitroquinoline in 64% yield as a yellow solid.
References
[1] Patent: WO2009/23844, 2009, A2. Location in patent: Page/Page column 112
[2] Patent: WO2010/21797, 2010, A1. Location in patent: Page/Page column 75-76
[3] Patent: WO2010/24980, 2010, A1. Location in patent: Page/Page column 93; 94
[4] ChemMedChem, 2018,
[5] Australian Journal of Chemistry, 2003, vol. 56, # 1, p. 39 - 44
