3-Pyridinecarboxaldehyde → HCID 86759539, compound

Participants

Reaction Steps

3-Pyridinecarboxaldehyde (0.550 g, 5 mmol) and 3-aminophenol (0.540 g, 5 mmol) were dissolved into methanol (15 ml). To the solution was added a mixture of sodium cyanoborohydride (0.378 g, 6 mmol) and zinc chloride (0.408 g, 3.0 mmol) in methanol at room temperature. The reaction mixture was stirred for 2.5 h. Most of the methanol was evaporated under reduced pressure. Ice water was added to the residue. It was filtered and the layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated to give the title compound. 1H NMR: 8.53 (s,1H), 8.45 (d,1H,J=3.9 Hz), 7.72 (d,1H,J=7.8 Hz), 7.24-7.30 (m,2H), 6.95-7.01 (m1H), 4.27 (s,2H). MS calcd. 200.1; MS (M+1) 201.1.

Provenance & Evidence