Acetic Acid → beta-(Methylamino)-2-naphthaleneacrylonitrile

Beteiligte Stoffe

Reaktionsschritte

A solution of β-oxo-2-naphthalenepropionitrile (5.0 g, 0.0256 mol) in toluene is treated with methylamine hydrochloride ()2.6 g, 0.0384 mol), sodium acetate (3.15 g, 0.0386 mol) and a catalytic amount of acetic acid, heated at reflux temperature (fitted with a Dean Stark trap) for 6 hours, cooled, diluted with ethyl acetate and dilute hydrochloric acid. The organic phase is dried over Na2SO4 and concentrated in vacuo to give a residue which is triturated under hexanes to give the title compound as a yellow solid, 3.1 g (58% yield) mp 138° C., identified by IR, 1NHMR and mass spectral analyses.

Herkunft & Nachweise