Aniline → HCID 56926180, compound

Participants

Reaction Steps

To a solution of 2,2-dimethyl-2H-pyrano[3,2-b]pyridine-6-carbaldehyde (434 mg, 2.28 mmol) in methanol (3 mL) was added aniline (0.3 mL, 2.52 mmol) and zinc chloride (621 mg, 4.56 mmol) and stirred at room temperature for 2 hours. Then NaCNBH3 (287 mg, 4.56 mmol) was added and stirred overnight. Purification by column: 4:1 Hx/EtOAc to give an off-white solid. Yield: 48%. 1H NMR (CDCl3) δ 1.49 (s, 6H), 4.361 (s, 2H), 5.91 (d, 1H, J=10), 6.55 (d, 1H, J=10), 6.68-6.71 (m, 3H), 7.01 (d, 1H, J=8.4), 7.08 (d, 1H, J=8.4), 7.18-7.38 ppm (m, 2H).

Provenance & Evidence