2-Chloro-3-cyanoquinoline

Synthesis

General procedure for the synthesis of 2-chloro-3-cyanoquinoline from 2-chloro-3-quinolinecarboxaldehyde: 2-chloroquinoline-3-carboxaldehyde (0.01 mol) was suspended in 30% ammonia (30 mL) and stirred at room temperature for 5 min to form a turbid solution. Stirring was continued at 0 °C and ceric ammonium nitrate (0.01 mol) was slowly added. The reaction process was monitored by thin layer chromatography (TLC) and the reaction time was about 10-15 minutes. After completion of the reaction, the reaction mixture was extracted with a solvent mixture of chloroform-ethyl acetate (5:3 v/v). The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was recrystallized by ethanol to give pure 2-chloro-3-cyanoquinoline as light yellow crystals in 82% yield.

References

[1] Synlett, 2009, # 20, p. 3378 - 3382
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1868 - 1875
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 1, p. 292 - 296
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 1, p. 152 - 154
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 3, p. 602 - 611