Sodium Carbonate → 8-Chloro-3-methyl-5,6,7,8-tetrahydroquinoline

To 7.02 g of 3-methyl-5,6,7,8-tetrahydroquinoline was added dropwise 9.62 g of methanesulfonyl chloride under ice-cooled condition. The reaction mixture was stirred under ice-cooling condition for 2 hours, then further stirred at 80° C. for 3 hours. To the reaction mixture was added water, and this solution was made alkaline by adding sodium carbonate, then extracted with diethyl ether. The diethyl ether layer was washed with an aqueous solution saturated with sodium chloride, and dried with anhydrous magnesium sulfate. The solvent was removed by evaporation, then thus obtained residue was purified by a silica gel column chromatography (eluent: dichloromethane/methanol=100/1) to obtain 2.74 g of 3-methyl-8-chloro-5,6,7,8-tetrahydroquinoline.

1. temperaturecooled condition
2. temperaturecooling condition for 2 hours
3. stirringfurther stirred at 80° C. for 3 hours
4. extractionextracted with diethyl ether
5. washThe diethyl ether layer was washed with an aqueous solution saturated with sodium chloride
6. dry with materialdried with anhydrous magnesium sulfate
7. customThe solvent was removed by evaporation
8. customthus obtained residue was purified by a silica gel column chromatography (eluent: dichloromethane/methanol=100/1)

ORD record

ord-f9a402c61f094f20878fb785d8903797

Source dataset

uspto-grants-1989_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04880815