Sulfuric Acid → 7-iodo-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

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Reaction Steps

A 1 N sulfuric acid aqueous solution (30 ml) and sodium nitrite (862.5 mg, 12.5 mmol) were added at 0° C. to an acetic acid solution (15 ml) that contained the 7-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (1.52 g, 5.0 mmol) obtained in step C, and the obtained mixture was stirred for 30 minutes. Thereafter, sodium iodide (2.62 g, 17.5 mmol) and copper iodide (I) (952.3 mg, 5.0 mmol) were added to the reaction solution, and the obtained mixture was stirred at 80° C. for 1 hour. The reaction solution was cooled, and a saturated sodium bicarbonate aqueous solution was added thereto, followed by extraction with ethyl acetate. The extract was washed with a saturated saline solution, and was then dried over anhydrous sodium sulfate, followed by concentration. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4 to 1:2). The resultant was washed with a sodium thiosulfate aqueous solution, so as to obtain 7-iodo-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (1.87 g; yield: 90%) in the form of a pale yellow solid.

Provenance & Evidence