Reaction Steps
A solution containing 0.4 g of N-propyl-N-quinol-5-ylthiourea (Compound 31) and 0.5 g of 2-bromo-1-(4-chloro-2-methoxyphenyl)propan-1-one in 15 ml of ethanol is heated at reflux for 6 hours. The reaction mixture is evaporated to dryness and then, successively, the residue is taken up in water, basified with 33% sodium hydroxide and extracted with ethyl acetate. The residue is purified on a column of silica gel eluted with a 1/1 (v/v) ethyl acetate/hexane mixture, to provide 0.46 g of a yellow oil. 1H NMR (CDCl3): 0.91 (t, J=7.3, 3H, --CH3), 1.61-1.78 (m, 2H, --CH2 --CH3), 2.02 (s, 3H, heterocycle --CH3), 3.83 (s, 3H, --OCH3), 3.97 (t, J=7.5, 2H, --CH2 --N<), 6.88 (dd, J=2.5, J=8.4, 1H, H5), 7.0 (d, J=2.5, 1H, H3), 7.36 (d, J=8.5, 1H, H6), 7.46 (dd, J=4.2, J=8.6, 1H, H3,), 7.63 (d, J=7.2, 1H, H4,), 7.80 (t, J=7.9, 1H, H7,), 8.17 (d, J=8.4, 1H, H6,), 8.33 (d, J=8.4, 1H, H8,), 8.96-8.99 (m, 1H, H2,).
