Acetonitrile → 3-CHLORO-4-NITRO-1H-INDOLE

Reaktionsgleichung

[Cl:1]N1C(=O)CCC1=O.[N+:9]([C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[CH:15][NH:16]2)([O-:11])=[O:10].C(#N)C>C(Cl)Cl>[Cl:1][C:14]1[C:13]2[C:17](=[CH:18][CH:19]=[CH:20][C:12]=2[N+:9]([O-:11])=[O:10])[NH:16][CH:15]=1

Komponenten

Versuchsvorschrift

N-Chlorosuccinimide (1.23 g, 9.25 mmol) is added to a solution of 4-nitroindole (1.5 g, 9.25 mmol, Aldrich) in methylene chloride (75 mL). The resulting mixture is heated to reflux for 16 hours. Acetonitrile (10 mL) is added to the mixture and heating is continued for another 16 hours. The reaction is cooled to room temperature and the methylene chloride is removed by rotary evaporation. The residue is taken up in ethyl acetate and washed with water. The ethyl acetate layer is dried over magnesium sulfate, filtered and the solvents removed by rotary evaporation. The crude material is purified via silica gel column chromatography using 30% ethyl acetate/hexane as the eluent. The product containing fractions are combined and the solvents removed by rotary evaporation to yield 1.35 g of 3-chloro-4-nitroindole as an orange solid (74%).