4-(2-Acetamidoethyl)benzoic acid → 3-Aminobenzoic Acid

Participants

Reaction Steps

4-(2-Acetaminoethyl)-benzoic acid was reacted with nitrating acid to 4-(2-acetaminoethyl)-3-nitro-benzoic acid, M.p. 189° C. (from methanol). The following catalytical hydrogenation yielded the 4-(2-acetaminoethyl)-3-aminoethyl)-3-amino-benzoic acid with a melting point of 143° C. (from ethanol/petroleum ether). From this compound, there was obtained by diazotation and Sandmeyer-reaction the 4-(2-acetamino-ethyl)-3-chloro-benzoic acid having a melting point of 150° C. or by boiling up the diazo solution, the 4-(2-acetaminoethyl)-3-chloro-benzoic acid M.p. 222°-223° C. From 4-(2-acetaminoethyl)-3-hydroxy-benzoic acid, there were obtained with dimethyl sulfate or diethyl sulfate, the corresponding 4-(2-acetaminoethyl)-3-methoxy-benzoic acid methyl ester and the 4-(2-acetaminoethyl)-3-ethoxy-benzoic acid ethyl ester.

Provenance & Evidence