Indole-3-acetonitriles, tryptamines from

Tryptamines can also be prepared from gramine via indole-3-acetonitriles. This procedure was found advanta ous for C-ha o tryptamines[9]. 

To the Grignard reagent prepared from 2.4 g Mg, 10 ml anisole and 16 g ethyl iodide, add 7.8 g indole in 10 ml anisole. Stir and cool to 0°. Slowly add dropwise 5.5 g Cl-acetonitrile in 40 ml anisole. Warm to room temperature and stir heat to 60-70° on water bath (a reddish precipitate forms over about twenty minutes). Cool and purify and convert to the dialkyltryptamine as described earlier. Tryptamines JOC 24,894(1959)... 

A solution of 6.0 g indole-3-acetonitrile in 15 mL anhydrous THF was added dropwise to 160 mL of a 1 M solution of LAH in THF, stirred and held under reflux conditions. After an additional 8 h reflux, the reaction was cooled, and the excess hydride and reaction complex were decomposed by the careful addition of wet THF until the evolution of hydrogen ceased, then 25 mL 5% aqueous NaOH was added, followed by sufficient H20 to leave the inorganic solids with a filterable texture (about 15 mL additional). These solids were removed by filtration, the filter cake washed with THF, the filtrate and washings combined, and the solvent removed under vacuum. The solid residue was recrystallized from CH3CN to provide 5.3 g (86%) tryptamine as a cream colored crystal with a mp 112-114 °C. IR (in cm-1) 751, 811,882, 941, 1014, 1112 and 1128. 

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