9-Bromo-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline

Chemical Properties

White Crystalline

Synthesis

The general procedure for the synthesis of 9-bromo-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline from julolidine: julolidine (675 mg, 3.90 mmol) and N-bromosuccinimide (832 mg, 4.68 mmol) were dissolved in 10 mL of N,N-dimethylformamide (DMF), and the reaction was stirred at room temperature for 5 hours. After completion of the reaction, the crude product was purified by silica gel column chromatography (eluent: hexane/dichloromethane, 3:1, v/v) to afford the target compound 9-bromo-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline (786 mg, 80% yield) as an oil. The structure of the product was confirmed by the following characterization: 1H NMR (500 MHz, CDCl3) δ/ppm: 6.87 (s, 2H), 3.10 (t, 4H, J=5.50 Hz), 2.70 (t, 4H, J=6.35 Hz), 1.94 (m, 4H); 13C NMR (500 MHz, CDCl3) δ/ppm: 142.0 ,129.3,123.7,107.3,50.0,27.6,21.9; IR (KBr, cm-1): 3045,2935,2836,1581,1506,1462,1446,1310; high-resolution mass spectrometry (TOFMS-EI) m/z: calculated value C12H14NBr [M]+ 251.0310 , measured value 251.0309.

References

[1] Chemical and Pharmaceutical Bulletin, 1984, vol. 32, # 5, p. 1770 - 1779
[2] Canadian Journal of Chemistry, 2009, vol. 87, # 2, p. 440 - 447
[3] Journal of Organic Chemistry, 2011, vol. 76, # 22, p. 9391 - 9408
[4] Dyes and Pigments, 2013, vol. 99, # 3, p. 653 - 660
[5] European Journal of Organic Chemistry, 2011, # 30, p. 6100 - 6109