Phosphorus oxychloride → 4-Benzyloxy-2-chloro-7-methoxy-8-methylquinoline

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Reaction Steps

POCl3 was added under inert atmosphere at −78° C. to 4-benzyloxy-7-methoxy-8-methylquinoline N-oxide (62, 2.5 g, 8.47 mmol). Then the reaction mixture was allowed to warm up to room temperature, then heated to reflux. After 35 min, the solution was cooled to room temperature and the excess of POCl3 was evaporated under reduced pressure. The residue was partitioned between ice-cooled water and AcOEt, dried (Na2SO4) and evaporated. The residue was triturated in ether, then filtered and successively washed with small portions of methanol and ether to give 2.4 g (90.4%) of the target product 63 as a white powder: m/z=314 (M+H)+.

Provenance & Evidence