Phosphorus oxychloride → 1-Chloro-6-methoxy-4-phenylisoquinoline-3-carbonitrile

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A mixture of 6-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonitrile (200 mg) and POCl3 (10 mL) was heated to 90 C for 18 h. The reaction was concentrated, and the residue was dissolve in EtOAc, cooled to 0 C, and quenched by careful addition of saturated aqueous sodium bicarbonate. The mixture was partitioned between saturated aqueous sodium bicarbonate and EtOAc. The aqueous solution was washed twice with EtOAc. The combined organic solutions were dried (Na2SO4) and concentrated. Flash chromatography (25 g silica, 3-30% EA/hex) gave a white solid.

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