Uses
1,2,3,4-Tetrahydro-6-methoxyquinoline is used as chemical reagents, organic intermediates, fine chemicals, pharmaceutical research and development.
Synthesis
GENERAL STEPS: 6-methoxyquinoline (1a; 65 mg, 0.5 mmol), Cu(OAc)2 (4.5 mg, 0.025 mmol), B2(OH)4 (135 mg, 1.5 mmol) and acetonitrile (2.0 mL) were added to a 20 mL Schlenk tube. The reaction mixture was stirred at 40 °C for 8 h. The progress of the reaction was monitored by TLC until the reaction was completed. After completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure. Water (10 mL) was added to the concentrated mixture, followed by extraction with ethyl acetate (3 x 10 mL). The organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography using petroleum ether/ethyl acetate (8:1) as eluent to afford the target product 6-methoxy-1,2,3,4-tetrahydroquinoline (2a: 65 mg, 98% yield) as a brown liquid.
References
[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3415 - 3418
[2] Advanced Synthesis and Catalysis, 2017, vol. 359, # 4, p. 677 - 686
[3] Advanced Synthesis and Catalysis, 2017, vol. 359, # 6, p. 933 - 940
[4] Chemistry - A European Journal, 2016, vol. 22, # 48, p. 17151 - 17155
[5] ChemCatChem, 2017, vol. 9, # 13, p. 2496 - 2505
