Acetic Acid → 4-(4-Chlorophenyl)-1,3-dihydro-indol-2-one

Temperature

27 °C

To the suspension of 4-(4-chloro-phenyl)-1H-indole (1.52 g, 6.68 mmol) in t-BuOH-ethanol-acetic acid (3:2:1) (81 mL) was added pyridinium tribromide (90% purity from Aldrich, 7.12 g, 20.0 mmol)) portionwise. The mixture was stirred at 27° C. for 3 hours, and then to the mixture was added acetic acid (30 mL). Zinc dust was added to the reaction mixture portionwise until the color changed from deep red to light yellow, and the reaction mixture was stirred at room temperature for one hour. The unreacted zinc dust was filtered off and washed with ethanol. The filtrate was concentrated, and the syrupy residue was suspended in water (500 mL) for 0.5 hour. The solid product was precipitated out, filtered, and washed repeatedly with water to remove the zinc salt and pyridine salt. After high vacuum dry, a pure product (1.54 g, 94%) was obtained.

1. stirringwas stirred at room temperature for one hour
2. filtrationThe unreacted zinc dust was filtered off
3. washwashed with ethanol
4. concentrationThe filtrate was concentrated
5. waitthe syrupy residue was suspended in water (500 mL) for 0.5 hour
6. customThe solid product was precipitated out
7. filtrationfiltered
8. washwashed repeatedly with water
9. customto remove the zinc salt and pyridine salt
10. customAfter high vacuum dry

ORD record

ord-57ba1cd7db1843788a9385f07cc8d66b

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06861418B2