Hydrochloric Acid → HCID 10064943, compound

Participants

Reaction Steps

To 678 mg (2.85 mmole) of ethyl valerate 2-furoylhydrazone dissolved in 3 ml of ethanol was added a solution of 514 mg (2.16 mmole ) of 4-nitrobenzylamine (generated from the hydrochloride by partitioning between ether and saturated Na2CO3 solution) in 3 ml of ethanol. The resulting solution was heated at 45°-50° C. for two hours and then at 70° C. overnight. The solution was cooled and concentrated. Column chromatography of the residue on silica gel (gradient elution with 0.5-2.5% methanol in CH2Cl2) afforded some recovered starting material (ester hydrazone) followed by 432 mg (61%) of the product as a yellow oil which upon standing at 5° C. crystallized to a solid having mp 91°-92.5° C., homogeneous by TLC in 97:3 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 327 (M+1)+.

Provenance & Evidence