Ethanol → HCID 44549262, compound

Participants

Reaction Steps

Concentrated sulfuric acid (768 mL) was added slowly to ethanol (1.6 L) with cooling (exothermic reaction!). 4-Methyl-5-nitropyridine-2-carbonitrile (62.4 g, 0.38 mol) was added to the cold solution. After the addition was complete, the solution was refluxed under nitrogen for 2 h. Part of the solvent (500 mL) was removed using an oil pump at 30° C. The remaining thick solution was poured onto ice (1 kg). After stirring for 15 min, the mixture was extracted with ether (2×1 L) and multiple times with dichloromethane. At first, the organic layer was the TOP layer. As the extraction continued, the organic layer changed from the top layer to the bottom layer due to change in density as less ethanol was extracted. The combined organic extracts were dried (magnesium sulfate) and concentrated. Recrystallization from hexanes yielded 44.4 g (56%) of the desired product. 1H NMR (300 MHz, CDCl3) δ ppm 1.46 (t, 3H, J=7.5 Hz), 2.71 (s, 3H), 4.51 (q, 2H, J=7.5 Hz), 8.13 (s, 1H), 9.22 (s, 1H). LCMS: (APCI, M+H+)=209

Provenance & Evidence