Acetic Acid → 3-Chloro-1-phenylisoquinoline-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

In an atmosphere of argon and at -5° C. 10.7 ml of a 20% diisobutylaluminum hydride solution in toluene are slowly added dropwise to 2.64 g of 3-chloro-4-cyano-1-phenyl-isoquinoline in 150 ml of absolute toluene. The mixture is stirred for 10 minutes at 0° C. and then hydrolized with a small amount of glacial acetic acid until the reaction is weakly acid. Next, water is added and the toluene phase is separated. The organic phase is washed successively with saturated sodium bicarbonate solution and with water, dried and the solvent is removed under reduced pressure. The residue is rubbed with ether and recrystallized from ethyl acetate.

Provenance & Evidence