Phosphorus oxychloride → HCID 17894863, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methyl-1,8-naphthyridin-2(1H)-one (440 mg, 2.75 mmol) in toluene was added 302 uL of POCl3 (1.2 eq). The resulting mixture was refluxed at 120° C. for 3 hours. After cooling to room temperature the reaction mixture was quenched into ice-H2O and extracted with EtOAc (3×10 mL). The combined organic extracts was washed with H2O (2×15 mL), brine (1×20 mL), and then dried over MgSO4. Concentration and purification by MPLC gave the desired 2-chloro-4-methyl-1,8-naphthyridine (330 mg, 67%). Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 2.72 (s, 3 H) 7.35 (d, J=1.17 Hz, 1 H) 7.53 (dd, J=8.20, 4.40 Hz, 1 H) 8.36 (dd, J=8.35, 1.90 Hz, 1 H) 9.10 (dd, 1 H).

Provenance & Evidence