Propanal → HCID 28445232, compound

Participants

Reaction Steps

5 g of 5-aminoquinoline, 3 ml of propionaldehyde and 4.7 g of para-thiocresol are dissolved in 100 ml of ethanol in a 250 ml round-bottomed flask. The reaction mixture is heated at reflux for 2 hours and then evaporated to dryness. The residue is dissolved in 100 ml of ethanol and cooled in an ice bath and then 6.5 g of sodium borohydride are added portionwise. When addition is complete, the reaction mixture is heated at reflux for 2 hours and then, successively, 30 ml of water are added, the mixture is basified with 20 ml of concentrated sodium hydroxide and stirred for 15 minutes and the organic solvents are evaporated. Extraction is carried out with dichloromethane and the organic phase is washed with water and then dried over sodium sulphate. The organic phase is evaporated to dryness and the residue is purified on a column of silica gel, eluent: ethyl acetate, to obtain 4 g of an oil which crystallizes. 1H NMR (CDCl3): 1.05 (t, J=3H, --CH3), 1.82-1.71 (m, 2H, --CH2 --CH3), 3.15-3.26 (m, 2H, --NH--CH2 --), 4.37 (sl, 1H, --NH--), 6.61 (dd, J=1.0, J=8.6, 1H, H4), 7.26 (dd, J=4.2, J=8.6, 1H, H6), 7.44-7.59 (m, 2H, H3, H2), 8.12 (dd, J=0.95, J=8.6, 1H, H8), 8.84 (dd, J=1.5, J=4.2, H2).

Provenance & Evidence