5-Amino-2-phenylindole

To a solution of 5-nitro-2-phenyl-1H-indole (2.83 g, 0.01 mol) in MeOH (30 mL) was added Raney Ni (510 mg) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered through a Celite pad and the filtrate was evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to give 2-phenyl-1H-indol-5-amine (1.6 g, 77percent). To a solution of 5-nitro-2-phenyl-1H-indole (2.83 g, 0.01 mol) in MeOH (30 mL) was added Raney Ni (510 mg) under nitrogen atmosphere. To a solution of 5-nitro-2-phenyl-1H-indole (2.83 g, 0.01 mol) in MeOH (30 mL) was added Raney Ni (510 mg) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered through a Celite pad and the filtrate was evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to give 2-Phenyl-1H-indol-5-amineTo a solution of 5-nitro-2-phenyl-1H-indole (2.83 g, 0.01 mol) in MeOH (30 mL) was added Raney Ni (510 mg) under nitrogen atmosphere.The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight.The catalyst was filtered through a Celite pad and the filtrate was evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to give To a solution of 5-nitro-2-phenyl-1H-indole (2.83 g, 0.01 mol) in MeOH (30 mL) was added Raney Ni (510 mg) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered through a Celite pad and the filtrate was evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to give 5a) (b) A mixture of 7.86 g. 5-nitro-2-phenylindole, 100 ml. absolute ethanol and 10 g. (wet weight) Grace No. 28 Raney nickel (previously washed with water and with absolute ethanol) is hydrogenated at ca. 3 atmospheres pressure and ca. 27° in a Parr apparatus. Hydrogen absorption ceases in ca. 3 hours and the reaction mixture, after dilution with ca. 300 ml. methylene chloride is filtered thru a Celite bed. The insolubles are washed with methylene chloride and with boiling ethanol. Removal of solvent from the combined organic solutions yields 6.51 g.

Molecular Weight:208.26
XLogP3:3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:208.100048391
Monoisotopic Mass:208.100048391
Topological Polar Surface Area:41.8
Heavy Atom Count:16
Complexity:235
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes