Aniline → 3-(2-Methylquinolin-4-yloxy)propyl bromide

Participants

Reaction Steps

A mixture of 2-methylquinolin-4-ol (1.59 g, 10 mmol) (synthesized from aniline and acetoacetic ester according to a procedure known in the art: see Leonard et al. (1946) J. Am. Chem. Soc. 68:1279-1281), 1,3-dibromopropane (8.08 g, 40 mmol) and potassium carbonate (1.659 g, 12 mmol) in acetone (50 mL) was refluxed until the starting material disappeared. The reaction mixture was filtered and after evaporation of solvent residue was purified by column chromatography on silica gel (1% MeOH: 99% CH2Cl2 as eluent). The product was obtained as light yellow solid (1.793 g, 64%). 1H NMR (400 MHz, CDCl3): 2.48 (2H, m), 2.69 (3H, s), 3.69 (2H, t, J=6.3 Hz), 4.33 (2H, t, J=5.8 Hz), 6.6 (1H, s), 7.43 (1H, t, J=7.5 Hz), 7.66 (1H, t, J=7.8 Hz), 7.95 (1H, d, J=8.5 Hz), 8.12 (1H, d, J=8.3 Hz).

Provenance & Evidence