Dimethyl Sulfoxide → HCID 19592223, compound

Participants

Reaction Steps

A mixture of 1-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (1.0 g, 4.3 mmol), DMSO (3 ml) and 4-cyanobenzylamine (1.2 g, 9 mmol) is heated on a steam bath for 3 hours, then is allowed to sit at room temperature overnight. The reaction mixture is poured into water and an oil separated. The oil is extracted with hot 10% ethanol/ethyl acetate, washed with water, and the organic layer is dried and evaporated. The residue is crystallized from ether/ethyl acetate and then is purified by recrystallization from ethyl acetate/hexane, followed by column chromatography on silca gel eluting with ethyl acetate and finally crystallization of the residue thus obtained from ethyl acetate/hexane to afford 280 mg of 1-ethyl-N-(4-cyanophenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as yellow crystals, m.p. 233°-234° C.

Provenance & Evidence