Methanol → 4-Hydroxy-1-methyl-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid [3-(3,4-dichlorophenyl)-propyl]-amide

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Reaction Steps

Reaction of N-[3-(3,4-dichlorophenyl)-propyl]-2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-acetamide (0.432 g, 1.20 mmol) with the paraformaldehyde-methylamine adduct in methanol using a procedure similar to the one described in the preparation of compound 44 (method 44B) gave 0.232 g (56% yield) of the title compound as white crystals; mp 157–158° C. (dec) (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm); 1.81 (2H, m, CH2), 2.57 (2H, t, J=7.5 Hz, CH2), 3.05 (3H, s, NCH3), 3.33 (2H, m, NCH2), 3.98 (2H, s, NCH2), 6.95 (1H, broad t, NH), 7.05 (1H, broad dd, aromatic), 7.21 (1H, d, J=2 Hz, aromatic), 7.26 (1H, d, J=8.1 Hz, aromatic), 10.13 (1H, broad, OH). Anal. Calcd for C5H16Cl2N2O3: C, 52.49; H, 4.70; N, 8.16. Found: C, 52.39; H, 4.80; N, 7.89.

Provenance & Evidence