Reacción #323550

Ecuación de reacción

N-chlorosuccinimide

1-methyl-7-benzoylindole

methylene chloride

N-chlorosuccinimide

→

1-methyl-7-benzoyloxindole

Disolventes

diethyl ether methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 2 hours
3. 3
   ConcentraciónThe reaction mixture was concentrated in vacuo and 52 ml
4. 4
   workup.ADDITIONof acetic acid added
5. 5
   workup.ADDITIONof 85% phosphoric acid was added
6. 6
   TemperaturaThe temperature was raised
7. 7
   Temperaturato reflux for 90 minutes
8. 8
   Temperaturathe reaction was cooled
9. 9
   workup.ADDITIONpoured into 200 ml
10. 10
    FiltraciónThe precipitate was filtered
11. 11
    workup.DISSOLUTIONdissolved in methylene chloride
12. 12
    Secadothe solution dried with magnesium sulfate
13. 13
    OtroRemoval of the solvent
14. 14
    Otrogave a residue which
15. 15
    Filtraciónfiltered through silica gel
16. 16
    OtroThe fractions were collected
17. 17
    Concentraciónconcentrated
18. 18
    Otroto give 4.0 g

Procedimiento

To a solution of 6.17 g. (26.25 mmoles) of 1-methyl-7-benzoylindole in 62 ml. of methylene chloride was added 3.58 g. (26.25 mmoles) of 98% N-chlorosuccinimide and the mixture allowed to stir for 90 minutes. An additional 720 mg. of N-chlorosuccinimide was added and stirring continued for 2 hours. The reaction mixture was concentrated in vacuo and 52 ml. of acetic acid added. The mixture was heated to 80° C. and 27 ml. of 85% phosphoric acid was added. The temperature was raised to reflux for 90 minutes and the reaction was cooled and poured into 200 ml. of ice and water. The precipitate was filtered, dissolved in methylene chloride and the solution dried with magnesium sulfate. Removal of the solvent gave a residue which was dissolved in 5% diethyl ether-methylene chloride and filtered through silica gel. The fractions were collected, combined and concentrated to give 4.0 g. of the product as a viscous oil.

Fuente