Carbon Tetrachloride → HCID 86706035, compound

Participants

Reaction Steps

A mixture of 2-methyl-1,5-naphthyridine (CAS#7675-32-3, Synchem-OHG #CDP146FP1, 998 mg, 6.92 mmol), NCS (1109 mg, 8.31 mmol), and benzoyl peroxide (84 mg, 0.347 mmol) in CCl4 (34 mL) was stirred at reflux for 17 h. The reaction mixture was checked by TLC (100% EtOAc). Volatiles were removed under reduced pressure and the residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried (MgSO4), and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on an Analogix IF-280 (Agilent SF15-24 g, 7:3 to 3:7 hexane/EtOAc). Fractions #7-8 were combined and concentrated under reduced pressure to give the undesired byproduct, 2-(dichloromethyl)-1,5-naphthyridine, as an off-white solid (113 mg, 7.7% yield). Fractions #12-18 were combined and concentrated under reduced pressure to give the desired 2-(chloromethyl)-1,5-naphthyridine as an off-white solid (472 mg, 38.2%). 1H NMR (300 MHz, CDCl3) δ 8.99 (dd, J=4.2, 1.6, 1H), 8.45 (d, J=8.8, 1H), 8.38 (ddd, J=8.5, 1.5, 0.8, 1H), 7.85 (d, J=8.7, 1H), 7.66 (dd, J=8.6, 4.2, 1H), 4.86 (s, 2H). MS (DCI—NH3) m/z=179 (M+H)+, m/z=196 (M+NH4)+, m/z=213 (M+NH4+NH3)+.

Provenance & Evidence