Sodium Carbonate → 1,2-Dihydro-4-[3-(dipropylamino)methyl-4-hydroxyphenyl]-5-hydroxy-1-oxoisoquinoline

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Reaction Steps

To a solution of the compound of Example 63 (84.6 mg, 222 μmol) in dichloromethane (5 mL) was added 1 mol/L boron tribromide-dichloromethane solution (1.11 mL, 1.11 mmol), and the mixture was refluxed for 24 hours. After cooling, the reaction mixture was poured in ice water and the solution was brought to pH 8 with sodium carbonate. This was extracted using dichloromethane, dried over anhydrous sodium sulfate, and then solvent was distilled off. The residue obtained was purified by Chromatolex NH column chromatography [ethyl acetate-methanol=20:1], thereby affording 69.8 mg of the title compound as colorless powder. Yield 86%.

Provenance & Evidence