N-Methylformanilide is used as a formylating reagent for certain organometallics. It is in combination with phosphoryl chloride used for Vilsmeier-Haack reactions and in heterocycle syntheses. Further, it acts as a swelling agent in the dyeing process of meta-aramid fibers.
21.4 mg (0.2 mmol) of N-methylaniline, 81.2 mg of ethyl bromodifluoroacetate (0.4 mmol), 2.5 mg (0.02 mmol) of cuprous acetate, 19.1 mg (0.04 mmol) of X-phos, and 32.7 mg (0.2 mmol) of cesium carbonate were added to 2 mLDMF solvent. The reaction was carried out at 110 C for 12 h. At the end of the reaction, it was cooled, filtered, and the filtrate was rotary evaporated to remove the solvent, and the residue was chromatographed on a silica gel column, drenched with a mixture of petroleum ether and ethyl acetate in a volume ratio of 8:1, the effluent was collected according to the actual gradient, detected by TLC, and the effluents containing the product were combined, and the solvent was removed by distillation in a rotary evaporator, and the solution was dried in vacuum to give the yellow liquid methanoylanilide 22.2 mg The yield was 82%.
