Sulfuric Acid → 5,6-Dimethoxy-1H-indole-3-ethylamine

Participants

Reaction Steps

A solution of AlH3 in THF was prepared by dropwise addition of a solution of 0.52 ml (0.98 g, 10 mmol) of 100% H2SO4 in 4 ml of THF to a mixture of 0.76 g (20 mmol) of LiAlH4 and 20 ml of THF. Without removing the precipitated Li2SO4, a solution of 0.5 g (2.33 mmol) of 5,6-dimethoxy-3-indoleacetonitrile in 4 ml of THF was added over 30 min period. after stirring for another hour, the excess hydride was destroyed by the addition of small chips of ice. Most of the supernatant THF solution was decanted (setting aside most of the THF at this point greatly reduces emulsion formation in the subsequent extraction). The precipitated aluminum salts were treated with cold 20% NaOH, and the resulting cloudy solution was extracted with CHCl3. These extracts were combined with the THF solution, washed with NaCl solution, and dried over Na2SO4. The solvents were removed, and the residue was triturated with Et2-pentane. The crystalline product was washed with hot Et2O-Skelly B and dried, giving 0.44 g (83%) of pure 5,6-dimethoxytryptamine.

Provenance & Evidence