Aluminium lithium hydride → 1H-Indole-3-ethanamine, 4-methoxy-

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Reaction Steps

Combine LiAlH4 (6.78 g; 178.74 mmol; 6 eq) and anhydrous THF. Dissolve 3-(2-nitrovinyl)-4-methoxy-1H-indole (6.5 g; 29.79 mmol) in anhydrous THF and add dropwise to the LiAlH4 solution with vigorous stirring. After the addition is complete, heat to reflux. After 1 hour cool to ambient temperature and stir. After 16 hours, quench the excess LiAlH4 as described in J. Med. Chem. 1995, 38, 2050. Filter the gray suspension through celite and rinse the celite with ethyl acetate. Evaporate the filtrate in vacuo to residue. Chromatograph the residue on silica gel eluting with 1 L of CHCl3MeOH/NH4OH (95:10:1) and then 1 L of CHCl3/MeOH/NH4OH (90:10:1) as the mobile phase. Pool fractions containing the product and evaporate to give the title compound as a tan solid: 1H NMR (300 MHz, d6-DMSO): 2.96 (t, 2H); 3.42 (t, 2H); 3.83 (s, 3H); 6.42 (dd, 1H); 6.93 (m, 3H); 10.7 (s, 1H); MS (ES+): m/z 191 (M+H)+; 174 (M−NH2)+; 159 (M−OCH3)+; (ES−): m/z 189 (M−H)−.

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