Hydrochloric Acid → HCID 22097533, compound

Participants

Reaction Steps

A mixture of 1-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (10 g, 0.043 mol), 4-methoxybenzylamine (13.0 g, 0.095 mol) and DMSO (75 ml) is heated at reflux overnight and then is allowed to stand for about 2 days. The reaction mixture is poured into ice water, and the resulting gum is treated with ethyl acetate. The product that oils out of the ethyl acetate is separated and then is dissolved in CH2Cl2. The CH2Cl2 layer is washed with water, then brine and then is dried over MgSO4 and evaporated under reduced pressure. The residue is dissolved in CH2Cl2 and purified by column chromatography on silica gel eluting with CH2Cl2 to afford the product as the free base. The free base is dissolved in methanol, and then is treated with methanolic HCl. A precipitate forms which is collected by filtration, washed with ether and dried in vacuo at 50° C. to afford 12.4 g of 1-ethyl-N-(4-methoxy phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine.HCl.1/2 H2O, m.p. 179°-180° C.

Provenance & Evidence