3-Chloroisoquinoline → 3-Ethoxyisoquinoline

Participants

Reaction Conditions

Reaction Steps

3-Chloroisoquinoline (3.0, 18 mmol) was dissolved in potassium ethoxide (24% in EtOH, 10.6 mL, 27 mmol) and heated to 150° C. in a sealed tube for 24 h. After cooling, the solvent was removed in vacuo and the residue treated with 1M HCl until the solution reaches a pH 3. Saturated NaHCO3 solution then added slowly to return the solution to pH 8 followed by extraction with CHCl3. The combined organics were washed with brine, dried over anhydrous MgSO4. The residue obtained from concentration in vacuo was purified by column chromatography on SiO2 (0-15% EtOAc, hex) to afford 1.5 g (48%) of 3-ethoxyisoquinoline. LCMS found 174.11 [M+H]+.

Provenance & Evidence