6-Chloro-1,2,3,4-tetrahydroquinoline

Uses

6-Chloro-1,2,3,4-tetrahydroquinoline (cas# 49716-18-9) is a compound useful in organic synthesis.

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 77, 1987 DOI: 10.1016/S0040-4039(00)95653-3

Synthesis

GENERAL STEPS: PdNPore (2.7 mg, 5 mol%) was dissolved in acetonitrile (5 mL) and 6-chloroquinoline (81.8 mg, 0.5 mmol) was added. The reaction mixture was placed in a magnetic stirrer at 30 °C for 16 h under hydrogen atmosphere (5 bar). After completion of the reaction, it was purified by column chromatography (silica gel, 200-300 mesh, ethyl acetate as eluent) to afford 6-chloro-1,2,3,4-tetrahydroquinoline (69.57 mg, 83% yield).

References

[1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 17, p. 7956 - 7967
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 50, p. 15656 - 15661
[3] Angew. Chem., 2016, vol. 128, # 50, p. 15885 - 15890,6
[4] Organic Letters, 2013, vol. 15, # 7, p. 1484 - 1487
[5] Chemical Communications, 2013, vol. 49, # 63, p. 7052 - 7054