6,7-dichloroquinoline-5,8-dione synthesis
- Product Name:6,7-dichloroquinoline-5,8-dione
- CAS Number:6541-19-1
- Molecular formula:C9H3Cl2NO2
- Molecular Weight:228.03
148-24-3
6541-19-1
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].
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Yield:6541-19-1 90%
Reaction Conditions:
with hydrogenchloride;sodium chlorate at 50 - 60; for 0.5 h;
Steps:
3 EXAMPLE 3, 6,7-dichloro-5,8-quinolindion of Formula 2
EXAMPLE 3 6,7-dichloro-5,8-quinolindion of Formula 2 After addition of 5-amino-8-hydroxyquinoline dihydrochloride (9 g) to hydrochloric acid (81 g), the reaction mixture was heated to 60° C. and NaClO3 (4.5 g) was added. The reaction mixture was stirred for 30 min at 50-60° C., filtered and recrystallized twice with buthanol to give yellow precipitate of 6,7-dichloro-5,8-quinolindion (90%).
References:
Il Jin Copper Foil Corp. US6818653, 2004, B1 Location in patent:Page column 5
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