Potassium Iodide → HCID 19008902, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-benzyloxy-naphthalen-1-ylamine (4.71 grams, 16.2 mmol) in DMF (25.0 mL) at room temperature was added NaH (372 mg, 16.2 mmol). After 0.5 h, 2-chloro-3-nitropyridine (5.53 grams, 35 mmol) and potassium iodide (2.8 grams, 17 mmol) were added. The reaction mixture was heated at 146° C. for 17 hours. The cooled solution was diluted with ether (300 mL) and the ether solution was washed with saturated aqueous NaCl (2×50 mL). The aqueous solution was extracted with CHCl3 (3×50 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo. The crude residue was chromatographed on SiO2 -gel using a gradient of 20% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to 3.0 grams of a yellow product. 1H NMR (250 MHz, CDCl3): d 8.63 (dd, 1H, J=1.65, 4.8 Hz), 8.58 (dd, 1H, J=1.7, 8.3 Hz), 8.41 (dd, 1H, J=1.73, 4.43 Hz), 8.23 (dd, 1H, J=1.63, 10.2 Hz), 7.93 (d, 1H, J=10 Hz), 7.75 (d, 1H, J=7.32 Hz), 7.68 (d, 1H, J=8.1 Hz), 7.26 (m, 6 H), 6.80 (dd, 1H, J=4.4, 8.1 Hz), 5.25 (s, 2 H).

Provenance & Evidence