Ethanol → HCID 18334159, compound

Participants

Reaction Steps

N-[(4-methoxyphenyl)-(3-nitrophenyl)methyl]benzamide (3.24 g) [prepared as described in step (c) above] was added in small portions to a 1:1 by volume mixture of ethanol and concentrated hydrochloric acid at ambient temperature. Tin (II) chloride (6.78 g) was then added in small portions to the mixture in an ice bath. The mixture was stirred at ambient temperature for 20 minutes and then heated under reflux for 2 hours. After cooling, the reaction mixture was neutralized with aqueous solution of sodium hydroxide and the insoluble material was removed by filtration using a Celite (trade mark) filter aid. The filtrate was extracted with ethyl acetate and the organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by chromatography through a silica gel column using a 2:1 by volume mixture of hexane and ethyl acetate as the eluant, to afford a colorless oil. This oil was dissolved in a solution of hydrogen chloride in ethyl acetate (4N) and the solvent was evaporated to dryness. The residual solid was suspended in diethyl ether and filtered, to afford the title compound (2.68 g) as a white solid.

Provenance & Evidence