Water → Ethyl 1,4-dichloro-7-isoquinolinecarboxylate

Participants

Reaction Steps

Anal. Found: C, 57.02; H, 3.99; N, 5.53. Calc for C12H10ClNO3 : C, 57.27; H, 4.01; N, 5.57. ##STR168## Ethyl 4-chloro-1-oxo-1,2-dihydro-7-isoquinolinecarboxylate (500 mg, 1.99 mmol) was warmed in POCl3 (3 mL) until a clear solution formed, and was then allowed to stand at 23° C. for 18 h. The reaction mixture was poured into warm water, extracted with EtOAc (3×20 mL), and the combined organic extracts washed with water and saturated brine, dried (MgSO4), and evaporated in vacuo. The residue was purified by column chromatography upon silica gel using hexane-EtOAc (90:10) as eluant followed by crystallisation from i-Pr2O to give ethyl 1,4-dichloro-7-isoquinolinecarboxylate (377 mg, 1.40 mmol) as a pale pink solid.

Provenance & Evidence