2-Nitroaniline → HCID 17810719, compound

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Reaction Steps

2-nitroaniline (829 mg, 6 mmol) and 1-methylindole carboxaldehyde (1242 mg, 7.8 mmol) were dissolved in 20 ml of tetrahydrofuran, to which acetic acid (200 μl) and NaBH(OAc)3 (5087 mg, 24 mmol) were sequentially added and stirred at room temperature overnight. A saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with ethyl acetate, dried with anhydrous sodium sulfate, and the solvent was evaporated. After purification by silica gel column chromatography (hexane:ethyl acetate=95:5), ((1-methylindole-3-yl)methyl)(2-nitrophenyl)amine was obtained (264 mg, yield 18%).

Provenance & Evidence