6146-52-7,6146-52-7, 5-Nitroindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
5-(Piperazin-1-yl)-1H-indole; A mixture of 5-nitro-1H-indole (34 g), palladium (5 wt %, dry basis) on activated carbon (2.5 g) and ethyl acetate was shaken at room temperature for 1.5 h under 3 atmospheres of hydrogen. The mixture was filtered, and the solvent was removed in vacuo to yield a solid (28 g), which was dissolved in tetrahydrofuran (400 mL). This solution was added to a boiling mixture of N-benzyliminodiacetic acid (54.4 g) and 1,1′-carbonyldiimidazole (82.4 g) in tetrahydrofuran (1100 mL), and the resulting mixture was boiled under reflux for 3 h. The mixture was filtered and concentrated in vacuo. The residue was purified by flash chromatography on silicagel (eluent: ethyl acetate/triethylamine 100:4) to give a solid (57.5 g), which subsequently was suspended in tetrahydrofuran (300 mL) and added to alane in tetrahydrofuran (500 mL) at 5-16 C. The alane was prepared from lithium aluminium hydride (25 g) and 96% sulphuric acid (32.3 g). The mixture was stirred at 5 C. for 45 min and subsequently quenched by addition of water (50 mL), 15% aqueous sodium hydroxide solution (25 mL) and water (125 mL). The mixture was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silicagel (eluent: ethyl acetate) to give a brown oily compound (44.9 g), which subsequently was dissolved in methanol (1000 mL). Ammonium formate (150 g) and palladium (5 wt %, dry basis) on activated carbon (12 g) was added, and the mixture was boiled under reflux for 45 min, cooled, filtered and concentrated in vacuo. The residue was dissolved in tetrahydrofuran/ethyl acetate and poured onto brine. Concentrated aqueous ammonia solution was added to the mixture under cooling to give an alkaline reaction mixture. The two phases were separated, and the aqueous phase was extracted twice with tetrahydrofuran/ethyl acetate. The combined organic phases were washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was precipitated from tetrahydrofuran/heptane to give the title compound (17.3 g).
As the paragraph descriping shows that 6146-52-7 is playing an increasingly important role.
Reference£º
Patent; Bang-Andersen, Benny; Larsen, Krestian; Mork, Niels; US2007/43058; (2007); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles