3-Pyridinecarboxaldehyde → HCID 178420771, compound

Participants

Reaction Steps

(See FIG. 10.) To a solution of nicotinaldehyde (2.0 mL, 21.2 mmol) in 95% EtOH (20 mL) was added 2-tosylhydrazine (3.95 g, 21.2 mmol) and the resultant solution was stirred at room temperature for 2 h. To the solution was added aqueous sodium hydroxide (5 N, 4.2 mL, 21.2 mmol) and the solution was stirred for twenty minutes. To the solution was added 1-vinylimidazole (9.6 mL, 106 mmol) and the resultant solution was warmed to 50° C. and stirred under an argon atmosphere for 96 h. The solution was poured into a water/EtOAc mixture (1:1, 100 mL), the organic fraction was collected and the aqueous fraction was extracted with EtOAc (2×50 mL). The combined organic fractions were dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (EtOAc/Hex, 50/50, Rf=0.08) to afford the title compound 27 (1.73 g, 56% yield) as a pale white oil: 1H NMR (CDCl3) δ 9.03 (m, 1H), 8.52 (m, 1H), 8.06 (m, 1H), 7.59 (d, J=2.2 Hz, 1H), 7.29 (m, 1H); 6.61 (d, J=2.5 Hz, 1H); LRMS (ESI) m/z calcd for C8H8N3 [M+H]+ 146. found 146.

Provenance & Evidence