5-Fluoroisatin → HCID 57475126, compound

Temperature

10 °C

5-Fluoroisatin 32 (10 mmol, Lancaster, order no. 14553) was dissolved in a mixture of ethanol/pyridine/acetic acid (50 ml, 15:5:2), ethyl potassium malonate 33 (1.87 g, 11 mmol) was added, and the mixture was heated under reflux for 14 hours. The course of the reaction was monitored by TLC (eluent: ethyl acetate/hexane 1:1). The product was worked up by distilling off the solvent mixture under reduced pressure, taking up the residue in ethyl acetate (50 ml) and extracting the mixture by shaking with water (50 ml). After separation of the phases, the aqueous phase was extracted twice with 30 ml portions of ethyl acetate. The combined organic phases were washed with 2 N HCl (50 ml), dried over Na2SO4 and concentrated to 20 ml under reduced pressure. Hexane was added to the solution until the product started to crystallize. To bring the crystallization to completion, the mixture was cooled to 10° C. for 12 hours. The solid was filtered out with suction and dried in vacuo.

1. additionwas added
2. temperaturethe mixture was heated
3. temperatureunder reflux for 14 hours
4. distillationby distilling off the solvent mixture under reduced pressure
5. extractionextracting the mixture
6. customAfter separation of the phases
7. extractionthe aqueous phase was extracted twice with 30 ml portions of ethyl acetate
8. washThe combined organic phases were washed with 2 N HCl (50 ml)
9. dry with materialdried over Na2SO4
10. concentrationconcentrated to 20 ml under reduced pressure
11. additionHexane was added to the solution until the product
12. customto crystallize
13. customthe crystallization to completion
14. filtrationThe solid was filtered out with suction
15. customdried in vacuo

ORD record

ord-ef1c16cdfd32408a8c05a021c53c3f92

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08124788B2