CC1[N:3]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[CH:11]3)C(C)=CC=1.Cl.NO.C(N(CC)CC)C.[OH-].[Na+]>CC(O)C.O>[NH2:3][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2A mixture of the 5-(2,5-dimethyl-1H-pyrrol-1-yl)-1H-indole (10.00 mmol), hydroxylamine hydrochloride (6.95 g, 100 mmol, 10 eq), and triethylamine (6.97 mL, 50.0 mmol, 5 eq) in 2-propanol (35 mL) and water (5 mL) was heated at reflux under nitrogen for a time depending on the substrate. The resulting reaction mixture was cooled, solid sodium hydroxide (4.00 g, 100 mmol, 10 eq) was added, and the resulting reaction mixture was stirred at room temperature under nitrogen for 24 hours. The reaction mixture was then filtered through Celite®, and the filtrate was evaporated under reduced pressure. The residue was column chromatographed using silica gel (approximately 100 g) and eluting with an appropriate solvent system to afford the appropriate 5amino-1H-indole.
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