Synthesis
General procedure for the synthesis of 6-nitro-1,2,3,4-tetrahydroquinoline from 6-nitroquinoline: in a 10 mL Schlenk tube, Fe(OTf)2 (0.005 mmol, 1.8 mg), 6-nitroquinoline (0.5 mmol, 72 mg), Hantzsch ester A (1.25 mmol, 318 mg) and 1.0 mL of CHCl3. The reaction mixture was stirred at 40 °C for 2 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography to afford the target product 6-nitro-1,2,3,4-tetrahydroquinoline (63.8 mg, 96% yield).
References
[1] Tetrahedron Letters, 2004, vol. 45, # 16, p. 3215 - 3217
[2] ChemCatChem, 2017, vol. 9, # 13, p. 2496 - 2505
[3] Tetrahedron Letters, 2017, vol. 58, # 36, p. 3571 - 3573
[4] Chemical Communications, 2018, vol. 54, # 62, p. 8622 - 8625
[5] Chemical Science, 2017, vol. 8, # 12, p. 8164 - 8169
