Water → HCID 89647849, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-dichloro-3-nitropyridine (3.86 g, 20 mmol), naphthalen-1-ylmethanamine (3.14 g, 20 mmol) and K2CO3 (4.14 g, 30 mmol) in DMF (100 mL) was stirred at 80° C. for 3 h. It was cooled to room temperature and poured into water (500 mL). It was extracted with EtOAc (300 mL×2). The combined organic layers were washed with brine (300 mL×3), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel eluted with EtOAc/Pet ether=1/6 to afford the desired product as a yellow solid (3.21 g, 51%); LC/MS: MS (ES+) m/e 314 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 5.21 (d, J=6.0 Hz, 2H), 6.80 (d, J=8.7 Hz, 1H), 7.43-7.63 (m, 4H), 7.85 (d, J=8.1 Hz, 1H), 7.97 (d, J=8.1 Hz, 1H), 8.26 (d, J=8.1 Hz, 1H), 8.46 (d, J=8.7 Hz, 1H), 9.20 (t, J=5.7 Hz, 1H).

Provenance & Evidence