Malonic Acid → HCID 10679395, compound

Participants

Reaction Steps

Alternatively, a solution of 1 (0.20 g, 1.30 mmol), malonic acid (0.68 g, 6.5 mmol) and piperidine (2 drops) in pyridine (2 mL) was stirred at room temperature at for 20 h and at 100° C. for 4 h, then 30% aqueous H2SO4 (10 mL) was added. The precipitate that formed was removed by filtration and washed with water to give (E)-1-methyl-4-nitro-2-pyrroleacrylic acid (2) as fine yellow needles (0.23 g, 92%). 1H NMR [(CD3)2SO] δ12.35 (br s, 1 H, CO2H), 8.13 (d, J=1.9 Hz, 1 H, H-5), 7.44 (d, J=15.9 Hz, 1 H, H-β), 7.41 (d, J=1.9 Hz, 1 H, H-3), 6.46 (d, J=15.9 Hz, 1 H, H-α), 3.79 (s, 3 H, NCH3). 13C NMR δ167.4 (CO2H), 135.3, 129.9 (C-2, 4), 130.6, 127.0, 118.6, 105.8 (C-3, 5, α, β), 34.8 (NCH3). Anal. Calculated for C8H8N2O4: C, 49.0; H, 4.1; N, 14.3. Found: C, 49.0; H, 4.0; N, 14.1%.

Provenance & Evidence