To a mixture containing 0.11 g (0.40 mmol) of 3-[(2,4-dimethylphenyl)amino]-1-methyl-5-nitropyridin-2(1H)-one in 50 ml of ethanol was added 0.062 ml (0.86 mmol) of propionaldehyde, 0.15 ml of glacial acetic acid and 0.15 g of 10% palladium on carbon (Degussa type, 50% wet). The flask was fitted with a balloon of hydrogen and allowed to stir at room temperature for 4 h. The reaction was filtered through GF/F paper and the filtrate concentrated under reduced pressure. The residue was purified via preparative HPLC to afford 5 mg (3.7%) of product.
