8-Hydroxyquinoline → HCID 135839353, compound

Participants

Reaction Steps

6,7-Dichloro-5,8-quinolinedione 2 was prepared in low yield from commercially available 8-hydroxyquinoline 1 by modification of a literature procedure (Shaikh, I. A.; Johnson, F.; Grollman, A. P. J. Med. Chem. 1986, 29, 1329). A solution of potassium cyanide (1.02 g; 16 mmol) in water (3 mL) was added to a boiling solution of the dichloroquinone 2 (794 mg; 3.48 mmol) in THF/methanol (1:1, 40 mL) and heating was continued for a further 2 min. The reaction mixture was concentrated to half-volume and diluted to the original volume with water. Hydrochloric acid (10 M) was added cautiously [Caution: HCN fumes] causing the reaction mixture to change from an olive-green solution to a pale brown suspension. The solid was filtered off, washed with water and air dried overnight thereby affording the dinitrile 3 as a chocolate-brown solid (509 mg, 69%). 1H NMR (CDCl3) δ 7.73 (1H, dd, J=8.6, 4.2 Hz), 8.75 (1H, dd, J=8.6, 1.5 Hz), 9.14 (1H, dd, J=4.2, 1.5 Hz), 13C NMR (d6-DMSO) δ 92.8, 93.1, 115.2, 115.4, 124.4, 125.1, 133.2, 141.1, 152.4, 152.6, 154.4.

Provenance & Evidence