Chloroacetyl chloride → 5-chloroacetyl-6-chlorooxindole

Temperature

75 °C

A mixture of 750 ml of dichloromethane, 150 g of 6-chlorooxindole, 161.6 g of chloroacetyl chloride and 477.2 g of aluminium chloride was refluxed for 9.5 hours. The reaction mass was quenched into a mixture of crushed ice and 135 ml of hydrochloric acid. The formed solid was filtered, and the wet compound was washed with water. The wet compound was dissolved in 3525 ml acetic acid by heating to 70 to 80° C., then carbon was added and the mixture was stirred briefly at the same temperature, and the carbon was removed by filtration and washed with 15 ml of acetic acid. The filtrate was allowed to cool to about 20° C. for solid formation. The solid was filtered, washed three times with 600 ml of water, and then dried to yield 148.5 g of the title compound.

1. temperaturewas refluxed for 9.5 hours
2. customThe reaction mass was quenched into a mixture of crushed ice and 135 ml of hydrochloric acid
3. filtrationThe formed solid was filtered
4. washthe wet compound was washed with water
5. dissolutionThe wet compound was dissolved in 3525 ml acetic acid
6. additioncarbon was added
7. customthe carbon was removed by filtration
8. washwashed with 15 ml of acetic acid
9. temperatureto cool to about 20° C. for solid formation
10. filtrationThe solid was filtered
11. washwashed three times with 600 ml of water
12. customdried

ORD record

ord-aa07fbf447b14e629b50ad77c7851c10

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07777037B2