Sulfuric Acid → HCID 12378147, compound

Participants

Reaction Steps

2,6-Diaminopyridine (16.4 g., 0.15 mole), 24 g. of benzoylacetone, 75 ml. of acetic acid and 1.5 ml of 96% sulfuric acid was refluxed with stirring for 24 hours. The solution was poured slowly with stirring into 50 g. of sodium hydroxide in 250 ml. of water; the temperature was held 20°-30° by cooling. The tan solid was filtered, washed well with water and dried, 21.8 g. One recrystallization from 100 ml. of 95% ethanol gave 6.9 g. of coarse needles, m.p. 65°-190°; a second recrystallization from 50 ml. of ethanol furnished 2.1 g. (6) of the title compound, m.p. 253°-255°; 1H nmr (deuteriochloroform+DMSO-d6, 60 MHz): δ2.67 (s,3H, CH3), 6.20 (broad exchangeable s, 2H, NH2), 6.92 (d, 1H, H5, J=9 Hz), 7.58 (d,1H, H6), 7.50 (m,3H,meta and para protons on C6H5), 8.30 (m,2H, ortho protons on C6H5).

Provenance & Evidence