Uses
6,?7-?Dichloroquinoline-?5,?8-?dione is a reagent used in the synthesis of pharmaceuticals, such as a platinum(II) complex with antitumor activity.
Synthesis
General procedure for the synthesis of 6,7-dichloroquinoline-5,8-dione from 8-hydroxyquinoline: sodium chlorate (0.50 mol) was slowly added to a solution of 8-hydroxyquinoline (0.10 mol) dissolved in concentrated hydrochloric acid (600 mL) over a period of 1 hour. The reaction mixture was stirred continuously at 40°C for 2 hours. Subsequently, the reaction solution was diluted with water to a total volume of 2 L. The resulting white precipitate was removed by filtration and discarded. The filtrate was extracted several times with dichloromethane (6 x 250 mL), all organic phases were combined, washed with water and concentrated under reduced pressure to give a yellow solid product. The solid product was recrystallized in methanol to give the final 6,7-dichloroquinoline-5,8-dione (compound 7) as bright yellow crystals. The characterization data of compound 7 was in agreement with that reported in literature [32].
References
[1] RSC Advances, 2015, vol. 5, # 78, p. 63330 - 63337
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 8, p. 4617 - 4625
[3] Journal of Medicinal Chemistry, 1986, vol. 29, # 8, p. 1329 - 1340
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 9, p. 3238 - 3251
[5] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 423 - 436
