Cyclohexanemethylamine → 1-ethyl-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

Participants

Reaction Steps

To a mixture of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]quinoline (10 g, 0.043 mol) and DMSO (75 ml) is added cyclohexanemethylamine (10.75 g, 0.095 mol). The reaction mixture is refluxed for about four hours, then is allowed to stand for about 2 days. About 40-50 ml of the DMSO is removed in vacuo and the residue is pured into ice waterl. A precipitate forms which is collected by filtration, washed with water and dried. The PG,13 solid precipitate is dissolved in CH2Cl2, washed with water, then brine and is then dried over MgSO4. The solvent is filtered and concentrated in vacuo and the residue is purified by column chromatography on silica gel eluting with ethyl acetate/cyclohexane (3/7) followed by recrystallization from hexane to afford 12 g (90.2%) of 1-ethyl-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as light yellow crystals, m.p. 161°-163° C.

Provenance & Evidence