Iodine → 2-Iodo-5-methyl-4-nitroaniline
Reaktionsgleichung
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])[NH2:5].[I:12]I>S([O-])([O-])(=O)=O.[Ag+2]>[I:12][C:6]1[CH:7]=[C:8]([N+:9]([O-:11])=[O:10])[C:2]([CH3:1])=[CH:3][C:4]=1[NH2:5]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
3-Methyl-4-nitroaniline was treated with iodine and silver sulfate to give 2-iodo-5-methyl-4-nitroaniline. Treatment of the nitroaniline with 2-(trimethylsilyl)acetylene under the typical Sonogashira conditions gave 5-methyl-4-nitro-2-[(trimethylsilyl)ethynyl]aniline, which was treated with a base in an aqueous methanolic solution to give 2-ethynyl-5-methyl-4-nitroaniline. A subsequent base-induced cyclization at an elevated temperature gave 5-nitro-6-methylindole, which was treated under a high pressure hydrogenation condition to provide 5-amino-6-methylindole.