HCID 12486248, compound → 3,4-Dihydro-2H-pyrano[3,2-b]pyridine

Participants

Reaction Steps

A solution of 2-(3-hydroxypropyl)pyridin-3-ol (0.90 g) in 48% hydrobromic acid (20 mL) in a sealed tube was heated at 150° C. for 5 h. The reaction mixture was cooled to rt, concentrated in vacuo and poured into a solution of NaOH in MeOH (1 M). The mixture was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 2:1 (v/v) PE/EA) to afford the title compound as pale yellow oil (0.24 g, 30.00%), HPLC: 92.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 136.3 (M+1); 1H NMR (400 MHz, CDCl3) δ: 7.99-7.98 (m, 1H), 7.19-7.11 (m, 2H), 4.19 (t, J=7.8 Hz, 2H), 2.91 (t, J=7.8 Hz, 2H), 2.12-2.07 (m, 2H) ppm.

Provenance & Evidence