Hydrochloric Acid → 1-(4-Aminophenyl)-1,2-cyclopropanedicarboxylic acid

Participants

Reaction Steps

20 g of 1-(4-nitrophenyl)-1,2-cyclopropanedicarboxylic acid are dissolved in 200 ml of ethanol and the solution is hydrogenated in the presence of 5% palladium on carbon. The suspension so obtained is diluted with methanol and the precipitated product is dissolved by addition of 1 equivalent of methanolic hydrochloric acid. A part of the solvent is stripped off in vacuo, then 1 equivalent of 2N sodium hydroxide solution is added and the mixture is evaporated to dryness. The residue is crystallised from water and dried in vacuo over KOH pellets at 60° C. The title compound (b) is obtained in the form of light brown crystals with a melting point above 230° C. and Rf=0.55 on thin-layer silica gel plates in the system methylene chloride/glacial acetic acid (20:10:2).

Provenance & Evidence