7-Methoxy-1,2,3,4-tetrahydroquinoline Chemical Properties

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

Appearance

Colorless to light yellow Liquid

7-Methoxy-1,2,3,4-tetrahydroquinoline Usage And Synthesis

Synthesis

General procedure for the synthesis of 7-methoxy-1,2,3,4-tetrahydroquinoline from 7-methoxyquinoline: platinum oxide (PtO2, 180 mg, 0.79 mmol) was added to a methanol (60 mL) solution of 7-methoxyquinoline (2.0 g, 12.56 mmol). Hydrogen (H2) was passed into the above solution at room temperature and the reaction mixture was stirred overnight. Upon completion of the reaction, the solid catalyst was removed by filtration. The filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using a petroleum ether solution of 3% ethyl acetate as eluent to afford 7-methoxy-1,2,3,4-tetrahydroquinoline as a light yellow oil (1.5 g). Mass spectrum (M + H)+ m/z: 164.0. 1H-NMR (300 MHz, CD3OD) δ: 6.76 (d, J = 8.4 Hz, 1H), 6.09-6.17 (m, 2H), 3.69 (s, 3H), 3.19-3.23 (m, 2H), 2.64-2.69 (t, J = 6.6 Hz, 2H), 1.85 -1.93 (m, 2H).

References

[1] Patent: WO2012/58125, 2012, A1. Location in patent: Page/Page column 115; 116
[2] Patent: WO2012/94462, 2012, A2. Location in patent: Page/Page column 83
[3] Patent: WO2016/86200, 2016, A1. Location in patent: Page/Page column 278
[4] Farmaco, Edizione Scientifica, 1954, vol. 9, p. 205,209
[5] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3415 - 3418

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