3-Chloro-6-(1-ethoxy-vinyl)-isoquinoline → 1-(3-Chloroisoquinolin-6-yl)ethanone

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Reaction Steps

A solution of 3-chloro-6-(1-ethoxy-vinyl)-isoquinoline (934 mg, 4 mmol) in 1,4-dioxane (10 mL) and hydrochloric acid (2 M, 5 mL) was stirred at room temperature for 30 minutes. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The organic extracts were combined, washed with water and brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography using a gradient of iso-hexanes/ethyl acetate 9:1 to 4:1 to afford the title compound (732 mg, 89%) as a white solid. 1H NMR (300 MHz, CDCl3) δ2.77 (s, 3H), 7.88 (s, 1H), 8.05 (d, J=8.5 Hz, 1H), 8.15 (dd, J=8.5, 1.4 Hz, 1H), 8.37 (br s, H), 9.17 (s, 1H). LCMS (m/z) 206/208 [M+H], Tr=4.40 min.

Provenance & Evidence