Hydrochloric Acid → HCID 20446157, compound

Temperature

80 °C

To a solution of ethyl 2-[2-amino-3-(2-fluorophenoxy)phenyl]acetate (8.5 g.) in dioxane (100 ml.) was added N-chlorosuccinimide (4.3 g.), and the mixture was stirred for an hour at 80° C. To the reaction mixture was added conc. hydrochloric acid (0.1 ml.), and the mixture was stirred for 10 minutes at ambient temperature. Dioxane was distilled off from the resulting mixture under reduced pressure. To the residue was added water and the mixture was extracted with ethyl acetate (200 ml.) twice. The extract was washed with a saturated aqueous solution of sodium chloride (100 ml.) twice, dried over magnesium sulfate and then evaporated under reduced pressure. The residue was washed with a mixture of diethyl ether and n-hexane (1:10) and recrystallized from ethanol to give crystals of 2-oxo-5-chloro-7-(2-fluorophenoxy)indoline (4.2 g.), mp 204° to 207° C.

1. stirringthe mixture was stirred for 10 minutes at ambient temperature
2. distillationDioxane was distilled off from the resulting mixture under reduced pressure
3. additionTo the residue was added water
4. extractionthe mixture was extracted with ethyl acetate (200 ml.) twice
5. washThe extract was washed with a saturated aqueous solution of sodium chloride (100 ml.) twice
6. dry with materialdried over magnesium sulfate
7. customevaporated under reduced pressure
8. washThe residue was washed with a mixture of diethyl ether and n-hexane (1:10)
9. customrecrystallized from ethanol

ORD record

ord-48ef1e8ff37242d3a63f5f479de274ac

Source dataset

uspto-grants-1984_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04472433