Acetic Acid → N,N'-Bis(salicylidene)ethylenediamine

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Reaction Steps

Ethylenediamine (5.71 g, 0.095 mmol) was dissolved into toluene (60 ml). To it, a catalytic amount of acetic acid was added. Then, salicylaldehyde (23.20 g, 0.190 mmol) dissolved into toluene (60 ml) was dropwise added into the above solution. The resulting solution was then stirred at room temperature overnight. A yellowish crystalline product was precipitated. It was filtered, washed with ethanol, and dried. The yield was 23.7 g (93%). 1H NMR (300 MHz, CDCl3): δ=3.84 ppm (s, 4H), 6.85 ppm (t, 2H), 6.92 ppm (d, 2H), 7.17 ppm (m. 2H), 7.19 ppm (m, 2H), 8.28 ppm (s, 2H), 12.77 (s, broad, 2×OH); ESI MS: calcd. for C16H16N2O2, 268.3, found 269.2 (M+1); UV/Vis (λmax, nm, in methanol): 212, 255, 316, 400; IR (cm−1, nujol mull): 1610 (m, —C═N—).

Provenance & Evidence