Reaction #2439947

Reaction equation

AlCl3

oxindole

HCl

4-nitrobenzoyl chloride

→

5-(4-Nitro-benzoyl)-1,3-dihydro-indol-2-one

Yield 96.0%

Solvents

water

DMF

DMF

DMF

Conditions

Workup

1. 1
   workup.ADDITIONoutside as this addition
2. 2
   Otherformed
3. 3
   TemperatureThe mixture was warmed to 50° C.
4. 4
   workup.STIRRINGstirred for 15 min at that temperature
5. 5
   OtherThe resulting reaction mixture
6. 6
   Temperaturewas heated to 90° C.
7. 7
   workup.STIRRINGto stir for 5 hours during which the reaction mixture
8. 8
   TemperatureThe reaction was cooled to room temperature
9. 9
   workup.ADDITIONIce was added directly to the flask
10. 10
    workup.STIRRINGthe contents were stirred at room temperature for 15 min
11. 11
    FiltrationThe precipitate was collected via vacuum filtration
12. 12
    OtherThe crude solid was purified
13. 13
    Washby washing with sat. NaHCO3(aq)

Procedure

AlCl3 (20.0 g, 150 mmol) was placed in a dry 200 mL round bottom flask and DMF (3.30 mL) was added dropwise at 0° C. During the addition of DMF care was taken to ensure that the reaction was allowed to vent to the outside as this addition caused an exotherm to occur. Additionally as the DMF was added a white suspension formed. This suspension was allowed to stir for 30 min at room temperature, after which 4-nitrobenzoyl chloride (2.984 g, 16 mmol) was added. The mixture was warmed to 50° C. and stirred for 15 min at that temperature. The 50° C. mixture then was treated with oxindole (2.051 g, 15 mmol). The resulting reaction mixture was heated to 90° C. and allowed to stir for 5 hours during which the reaction mixture turned from a yellowish suspension to a thick black oil. The reaction was cooled to room temperature. Ice was added directly to the flask followed by water, turning the black oil into a pale yellow/white precipitate. Concentrated HCl(aq) (3 mL) was added to the reaction and the contents were stirred at room temperature for 15 min. The precipitate was collected via vacuum filtration. The crude solid was purified by washing with sat. NaHCO3(aq) providing 5-(4-Nitro-benzoyl)-1,3-dihydro-indol-2-one as a gray solid (4.05 g, 14.4 mmol, 95%).

Source