Hydrochloric Acid → HCID 20329649, compound

Participants

Reaction Steps

A mixture of 3.0 g of 12B, 50 ml of 6 N hydrochloric acid and 50 ml of ethanol was stirred and refluxed for 5 hours. The solution was concentrated to about half its volume, the solid that formed was collected, and dissolved in chloroform containing some triethylamine. The solution was washed with water, dried (MgSO4) and filtered. The solvent was evaporated from the filtrate under reduced pressure. The residue was dry column chromatographed over silica gel, using a 1/9 v/v mixture of tetrahydrofuran and chloroform as eluent. The solvents were evaporated, the appropriate sections were combined and extracted with chloroform. The extract was filtered and the solvent was evaporated under reduced pressure. The residue was refluxed in petroleum ether for 8 hours. The mixture was filtered and the filtrate placed in a freezer overnight. The solid that formed was collected and dried to give ethyl 5-(4-aminophenyl)benzofuran-2-carboxylate (12C), mp: 95°-97° C.

Provenance & Evidence