Syntheses and methylations of 2,3-dioxopyrrolidines with different amines / Anis Raehana Bt Abd Rasid

In this research, sodium diethyl oxalate that has been used as the starting material was
reflux together with amine and 4-methoxy benzaldehyde for 30 minutes via one-pot
reaction. Two different amines which is benzyl amine and methyl amine were used
for the variation of the result. Then, the products forms via one-pot reaction were
being alkylated by using methyl iodide as the alkylating agent. The 2,3-
dioxopyrrolidine derivatives in ethanol was refluxed with the methyl iodide and
potassium carbonate. The expected alkylation was preferred at C4 position on the
pyrrolidine ring because the α-hydrogen is more acidic since it is surrounded by the
carbonyl carbon and benzene group. But the result obtained through the
characterization of 1H NMR spectrum show that there is O-alkylation instead of Calkylation.
The methyl group is attached to the oxygen at C3 position on the
pyrrolidine ring system. Chromatography analysis also has been proposed to identify
the present of other impurities. On the TLC, several spots were observed represent the
major product, some unreacted starting material and impurities product. The desired
product has been separated from the others material and product through the column
chromatography.