Methyl 3-isoquinolinecarboxylate → Isoquinoline-3-carboxaldehyde

Participants

Reaction Steps

A solution of methyl 3-isoquinolinecarboxylate (2.0 g, 10.7 mmol) in toluene was cooled to −78° C. To the solution was added diisobutylaluminum hydride (1M in toluene, 21.4 mL, 21.4 mmol) slowly over 15 minutes via syringe. While still at −78° C., the reaction was quenched with a solution of ether (80 mL), acetic acid (20 mL) and water (8 mL) and then the mixture was allowed to slowly warm to room temperature overnight. The organics were decanted and the solvent was evaporated. Flash column chromatography (gradient 1:4 ethyl acetate/hexanes to 1:3 ethyl acetate/hexanes) provided 1.1 grams of the title compound (65% yield). 1H-NMR (CDCl3, 300 MHz) δ 10.24 (s, 1H), 9.35 (s, 1H), 8.36 (s, 1H), 8.07-7.98 (m, 2H), 7.82-7.32 (m, 2H). Mass spec.: 158 (MH)+.

Provenance & Evidence