Chloroform → Methyl 6-bromo-2-methylquinoline-3-carboxylate

To DMF (7.18 ml) was dropwise added phosphoryl chloride (8.64 ml) at 0° C., and the mixture was stirred at room temperature for 30 minutes. To the mixture was added methyl acetoacetate (10 ml) at 0° C., and the mixture was stirred at room temperature for 2 hours. The mixture was cooled to 0° C., and to the mixture was added 4-bromoaniline (16.78 g), and the mixture was stirred at 90° C. for 4 hours. To the reaction mixture was added chloroform, and the mixture was neutralized with 8N sodium hydroxide. The organic layer was washed with water and saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:2) and was recrystallized from ethyl acetate-hexane to give methyl 6-bromo-2-methylquinoline-3-carboxylate (6.02 g) as pale yellow crystals.

1. customat 0° C.
2. stirringthe mixture was stirred at room temperature for 2 hours
3. temperatureThe mixture was cooled to 0° C.
4. stirringthe mixture was stirred at 90° C. for 4 hours
5. washThe organic layer was washed with water and saturated sodium chloride solution
6. dry with materialdried with magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was separated
9. custompurified with column chromatography (ethyl acetate/hexane=1:2)
10. customwas recrystallized from ethyl acetate-hexane

ORD record

ord-351ccd126c1c46c1997a49c895b542ee

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06172061B2