1-t-Butoxy-3-chloroisoquinoline → 3-CHLORO-2H-ISOQUINOLIN-1-ONE

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Reaction Steps

0.5 g (2.12 mmol) of 1-t-butoxy-3-chloroisoquinoline from example 16.3 was dissolved in 5.0 ml of formic acid and stirred at room temperature for 20 h. The solution was then diluted with 10 ml of H2O, and the precipitated solid was filtered off through a glass frit, washed with 10 ml of H2O/formic acid (2:1) and dried under high vacuum. 0.30 g (1.67 mmol, 78.8%) of 3-chloroisoquinolin-1(2H)-one was obtained. The combined aqueous phases were concentrated to dryness under reduced pressure and the resulting solid was purified by column chromatography (5:1 dichloromethane/ethyl acetate), whereupon a further 0.040 g (0.22 mmol, 10.4%) of 3-chloroisoquinolin-1(2H)-one was obtained.

Provenance & Evidence