Methanol → HCID 58228464, compound

2,6-Dichloroquinoline (30 g) and aluminium trichloride (60 g) were heated to 120° C. with stirring under a nitrogen atmosphere. Bromine (9.2 mL) was added dropwise over 1 hour and the mixture was then stirred at 120° C. for 1 hour before being cooled to room temperature. A methanol/deionised water mixture (150 mL, 1:1) was then slowly added and the mixture was concentrated in vacuo. Dichloromethane (500 mL) and deionised water (250 mL) were added, the layers were separated and the aqueous fraction was extracted with dichloromethane (2×250 mL). The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (250 mL) before being dried, filtered and concentrated. Purification by chromatography (SiO2, isohexane:dichloromethane 7:3 as eluant) gave the title compound as a solid (27 g).

1. stirringthe mixture was then stirred at 120° C. for 1 hour
2. additionwas then slowly added
3. concentrationthe mixture was concentrated in vacuo
4. additionDichloromethane (500 mL) and deionised water (250 mL) were added
5. customthe layers were separated
6. extractionthe aqueous fraction was extracted with dichloromethane (2×250 mL)
7. washThe combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (250 mL)
8. custombefore being dried
9. filtrationfiltered
10. concentrationconcentrated
11. customPurification by chromatography (SiO2, isohexane:dichloromethane 7:3 as eluant)

ORD record

ord-8a444ee71c2f4a088eff9c2b2f9e1fe7

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07408065B2