合成路线1

The condensation of 4-nitrophenylacetonitrile (I) with diethyl carbonate by means of sodium ethylate in toluene gave the intermediate arylcyanoacetate sodium salt (II) that was further alkylated with 1,4-dibromobutane (III) to yield the bromobutyl derivative (IV). Subsequent treatment of bromide (IV) with diethylamine provided amine (V). Decarbethoxylation of the cyanoester group of (V) to give (VI) was carried out using aqueous KOH in the presence of benzyltriethylammonium chloride. Partial hydrolysis of the nitrile group of (VI) by means of potassium hydroperoxide in DMSO afforded amide (VII). This was subjected to Hoffman rearrangement by means of Br2 and NaOEt to produce carbamate (VIII), which was subsequently hydrolyzed to amine (IX) with KOH. This was finally coupled with benzoyl chloride to furnish the title benzamide.