2-[4-(Aminomethyl)phenyl]benzonitrile → 4'-[(3-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)methyl]biphenyl-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 400 mg (1.923 mmole) of [(2'-cyanobiphenyl-4-yl)methyl]amine, 457 mg (2.12 mmole) of ethyl valerimidate carbethoxyhydrazone (from Example 2, Step A), and 7 mL of ethanol was stirred under N2 in an oil bath at 50° C. for 3 hours and then at 80° C. for 2 days. The mixture was cooled and concentrated. The residue, re-concentrated from toluene, was flash chromatographed over silica gel (gradient elution with 1.5-5% methanol in CH2Cl2) to give 591 mg (93%) of desired product, homogeneous in TLC (90:10 CH2Cl2 --MeOH); mass spectrum (FAB) m/e 333 (M+1)+.

Provenance & Evidence