Dimethylformamide → 3-Azaisatoic anhydride

Participants

Reaction Steps

A 100 ml. flask was charged with 2.0 g. 2-carbamylnicotinic acid* suspended in 20 ml. dimethylformamide. A 5.5 g. portion of lead tetra-acetate was added to the suspension, and the mixture was stirred at 50°-60° for 1 hour. The reaction mixture was poured into 20 ml. water; solids were separated by filtration, and 3-azaisatoic anhydride was recrystallized from dioxane, and dried in vacuo for 2 hours. The final yield of 3-azaisatoic anhydride amounted to 1.48 g., melting point 217°-219°, and represented 75 percent of theory. The structure was confirmed by elemental analysis and infrared spectroscopy.

Provenance & Evidence