6,7-dichloroquinoline-5,8-dione

Sodium chlorate (0.50 mol) was added over a period of 1 h to a solution of 8-hydroxyquinoline (0.10 mol) in concd HCl (600 mL) at 40 °C and the reaction mixture stirred for 2 h before being diluted with water to a total volume of 2 L. Quinoline Phthalocyanine; a) 6, 7-dicyano-5, 8-dihydroxyquinoline 3; 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, 69percent).EXAMPLE 3

Molecular Weight:228.03
XLogP3:2.4
Hydrogen Bond Acceptor Count:3
Exact Mass:226.9540837
Monoisotopic Mass:226.9540837
Topological Polar Surface Area:47
Heavy Atom Count:14
Complexity:338
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes