Sodium Acetate → Isopropyl 2-amino-1,4-dihydro-5-cyano-6-methyl-4-(3-phenyl-quinolin-5-yl)-pyridine-3-carboxylate

Participants

Reaction Steps

4.66 g (20 mmol) of 3-phenyl-quinoline-5-aldehyde are boiled in 40 ml of isopropanol with 1.64 g (20 mmol) of 3-aminocrotononitrile, 3.6 g (20 mmol) of isopropyl amidinoacetate hydrochloride and 1.64 g (20 mmol) of sodium acetate for 20 hours. The mixture is concentrated, the residue is taken up in ethyl acetate/water and the phases are separated. The organic phase is washed twice with water, dried and concentrated. The reaction mixture is separated over a silica gel column using methylene chloride/ethyl acetate mixtures. The desired fractions are collected and concentrated. The resulting evaporation residue is crystallised with acetonitrile and filtered off with suction 635 mg of colourless crystals of melting point 227°-229° C. are obtained.

Provenance & Evidence