Water → 4-Hydroxyquinoline-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

The 4-(1H)-quinolone-3-nitrile (12 g) and sodium hypophosphite (16.12 g) were dissolved in a mixture of acetic acid:water:pyridine=125 ml: 125 ml:250 ml and 4 g of Raney Nickel (W2 grade) added (Backeberg and Staskim, J.C.S. 1962, 3691). The reaction mixture was heated at 60° C. for four hours, then the hot suspension was filtered and the catalyst cake washed with warm ethanol into the filtrates. The combined filtrates and washings were evaporated to one-third of the original volume and on equal volume of water added. The precipitated solid was filtered off, washed with water and dried to give the required 3-formyl compound as a light-brown solid, m.p. 268°-270° C. (3-formyl-4(1H)-quinolone).

Provenance & Evidence