Acetic Acid → 2-Methylfuran-3-carboxamide

Participants

Reaction Steps

To the solution of 1,1-dimethylhydrazine (0.6 mL) in methanol (15 mL) was added, in portions, a suspension of N-(4-chloro-3-formylphenyl)-2-methyl-3-furancarboxamide (2 g) in methanol (30 mL) at such a rate that the temperature of the solution was maintained at -5° C. to 0° C. The resultant mixture was stirred overnight at ambient temperature. Acetic acid (0.1 mL) was then added to the reaction mixture which was then refluxed for 30 minutes, solvent was evaporated and the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried (MgSO4) filtered and evaporated to produce N-[4-chloro-3-[dimethylhydrazono)methyl]phenyl]-2-methyl 3-furancarboxamide as a white solid, m.p. 109-111° C.

Provenance & Evidence