HCID 66704013, compound → HCID 66704005, compound

Participants

Reaction Steps

570 mg of 6-chloro-2-(N-acetyl-N-ethylamino)-4-(4-nitrophenyl)quinoline were suspended in 11.4 ml of THF and, under argon, added in portions to 3.1 ml of borane-THF complex. The temperature rose to 30° C. After stirring at room temperature for 3 hours, the solvent was removed by distillation and the residue was mixed with 50 ml of ethanol and 20 ml of concentrated HCl and heated on a water bath, cooled and distilled to remove the water. The residue was mixed with water, made alkaline with 2N NaOH, extracted with ethyl acetate and washed with water. The product was purified by MPLC chromatography using an MPRC cartridge with a mixture of 10 parts by volume of ethyl acetate, 5 parts by volume of n-heptane, 5 parts by volume of dichloromethane, 5 parts by volume of methanol and 1 part by volume of concentrated aqueous ammonia solution. A yellow solid product was isolated.

Provenance & Evidence