3-Phenylquinoline-5-carbonitrile → 3-Phenyl-5-hydroxymethylquinoline

Participants

Reaction Conditions

Reaction Steps

23 g (0.1 mol) of 3-phenylquinoline-5-carbonitrile (substance from Example 4) are admixed in 150 ml of formic acid with 10 g of Raney nickel. The mixture is stirred for about 5 hours at about 80° C. The slow formation of 3-phenylquinoline-5-carbaldehyde is observed by means of HPLC. In addition, 3-phenyl-5-hydroxymethylquinoline is formed as overreduced product. For the work-up, 300 ml of H2O are stirred in and the mixture is optionally extracted with 200 ml of methylene chloride. The methylene chloride phase is subsequently stirred at 40° C. (reflux) for 2 hours with 10 g of manganese dioxide. After filtration, the solution is evaporated and the residue is recrystallized from isopropanol.

Provenance & Evidence