3-(2-Morpholin-4-ylethoxy)benzaldehyde → 5-iodo-N-[(E)-[3-(2-morpholin-4-ylethoxy)phenyl]methylideneamino]pyridin-2-amine

Participants

Reaction Steps

To a suspension of 5-iodo-2-hydrazinopyridine (6.62 g, 0.028 mmol) in EtOH (90 mL) was added 3-(2-morpholin-4-yl-ethoxy)-benzaldehyde (6.63 g, 0.028 mmol). The reaction was heated at reflux for 2 h under nitrogen, then cooled to RT. The resulting precipitate was collected by filtration and washed with EtOH to afford the title compound (10.93 g, 86%) as a white solid. LCMS (Method 1): Rt 2.37 min, m/z 453 [MH+]. 1H NMR (300 MHz, CD3OD): δ 8.24 (1 H, d, J 2.2), 7.90-7.84 (2 H, m), 7.36-7.18 (3 H, m), 7.12 (1 H, d, J 8.8), 6.94-6.89 (1 H, m), 4.19 (2 H, t, J 5.4), 3.72 (4 H, t, J 4.6), 2.83 (2 H, t, J 5.4), 2.62 (4 H, t, J 4.6).

Provenance & Evidence