Formaldehyde → N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of 2 M methylamine in tetrahydrofuran (0.5 ml, 1.0 mmol) was added to a mixture of paraformaldehyde (0.3 g, 1.0 mmol, equivalent of formaldehyde) in anhydrous ethanol (1 ml) and the resulting mixture was heated at 60° C. for 5 min. Then a solution of 3-[(3,4-dichlorobenzyl)-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (0.318 g, 1.0 mmol) in ethanol (3 ml) was added all at once and the resulting mixture was maintained at 60° C. for another 20 min. The reaction mixture was then quenched by the addition of ethyl acetate and pH 2 phosphate buffer. The organic phase was washed with brine, dried (anhydrous magnesium sulfate) and concentrated under reduced pressure. Recrystallization of the solid residue from a mixture of ethyl acetate and hexane gave 0.180 g (54% yield) of the title material as a white solid: mp 148–150° C.

Provenance & Evidence