Reaction of β-Ethoxyacrolein and p-Toluidine in Benzene Solution

Abstract

1-Ethoxy-3-(p-methylphenylimino)-1-propene (IV) was prepared to elucidate the reaction sequence in the formation of 1-(p-methylphenylamino)-3-(p-methylphenylimino)-1-propene (malonaldehyde dianil of p-toluidine) (III) from β-ethoxyacrolein (I) and p-toluidine. The reaction of I and p-toluidine in benzene solution was followed spectrophotometrically, and evidence was obtained for the existence of IV as an intermediate in the formation of III. Acetic acid acted as an effective catalyst for the formation of β-(p-toluidino) acrolein (II) from I and p-toluidine in benzene solution. β-(p-Nitroanilino) acrolein (VIII) and β-(4-pyridylamino) acrolein 1-oxide (IX) were prepared from I and the corresponding amines under acidic conditions.