Notes #

1. Procedure: (Example) 10 grams of harmaline dissolved in 10% aqueous hydrochloric acid had zinc dust added gradually (with occasional shaking). The mixture was heated on a water bath until the yellow coloration disappeared. After filtering off any unreacted zinc, ammonium chloride was added to prevent precipitation of zinc hydroxide. Addition of ammonia caused an immediate precipitation of white material. This was shaken into Ethyl acetate; which recovered THH. (See Siddiqui et al. 1983 for their version of this procedure.) (This should also work for harmine) Siddiqui et al. 1983 reported that the addition of NH4Cl prior to basification with Ammonia increased the yield for this reaction from 50% to around 80% (by preventing the precipitation of Zinc hydroxide).