3,5-Dinitroaniline → HCID 178467279, compound

Participants

Reaction Steps

Following the procedures of Example 4, an equimolar mixture of 3,5-dinitroaniline and 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one in methanol was reacted to give 5-acetyl-4-hydroxy-3-[1-(3,5-dinitrophenylamino)ethylidene]-2H-pyran-2,6(3H)-dione. A solution of the latter (3.0 g., 0.008 mol) in 30 ml. of dimethylformamide was hydrogenated over 200 mg. of 10% palladium-on-carbon at 50 psi. When absorption stopped the catalyst was filtered and the filtrate poured into 200 ml. of ice-water. The resulting product was filtered, washed with water and dried to give 5-acetyl-4-hydroxy-3-[1-(3,5-diaminophenylamino)ethylidene]-2H-pyran-2,6(3H)-dione, m.p. above 350° C. (dec.).

Provenance & Evidence