4-Methoxybenzyl alcohol → HCID 61709251, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-amino-2-chloropyridine (Aldrich) (1.000 g, 7.78 mmol) in 4-methoxybenzyl alcohol (Fluka) (9.66 mL, 78 mmol) was treated with sodium hydroxide (J. T. Baker) (0.584 mL, 31.1 mmol) and tetrabutylammonium iodide (Aldrich) (0.287 g, 0.778 mmol). The resulting mixture was heated at 160° C. under N2 for 2 h. The reaction mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×15 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (120 g, 20% to 30% acetone in hexanes) to give the product as a white solid (1.32 g). m/z (ESI, +ve ion) 231.1 (M+H)+. 1H NMR (300 MHz, CDCl3) δ 7.85 (d, J=5.70 Hz, 1H); 7.38 (d, J=8.18 Hz, 2H); 6.91 (d, J=8.48 Hz, 2H); 6.22 (d, J=7.02 Hz, 1H); 5.99 (s, 1H); 5.27 (s, 2H); 4.04 (br. s., 2H); 3.82 (s, 3H).

Provenance & Evidence