Dimethyl Sulfoxide → 3-Butyryl-4-(o-tolylamino)quinoline-8-carbaldehyde

Participants

Reaction Steps

Oxalyl chloride (18.22 g, 0.144 mol) in dichloromethane (180 ml, dried over molecular sieves) was cooled to -70° C., and a solution of dimethylsulphoxide (13.08 g, 0.168 ml) in dry dichloromethane (20 ml) added dropwise under nitrogen with stirring, keeping the temperature below -60° C. After 30 minutes, a solution of 3-butyryl-4-(2-methylphenylamino)-8-hydroxymethylquinoline (40 g, 0.12 mol) in dry dichloromethane (700 ml was added dropwise below -60° C. After a further 30 minutes, triethylamine (102 ml) was added dropwise, and the mixture allowed to warm to room temperature, washed with water and dried (Na2SO4). The filtered solution was evaporated to a yellow oil, which crystallized on trituration with ether to give the title compound (33.02 g), m.p. 142°-4°.

Provenance & Evidence