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Yield, 90%. This is a gentle reduction made from Tyramine, but it can be used on most any reducible forms. See the amphetamines chapter for formula (JACS, 72, 2781, 1950) of 4-hydroxy-3-methoxy-B-nitrostyrene and analogs. For a reduction using the reverse addition of LAH and several other reductions see the amphetamine chapter. A Reduction With Aluminum Hydride (Alane). 8 g) of LAH and 100 ml of dry ether. 3 g) of aluminum chloride (dry or anhydrous) rapidly through the dropping funnel, continuing the stirring the entire time.
After the reaction is over, the zinc is filtered off, care being taken not to let it become dry, as it is pyrophoric. Also, be careful while disposing of zinc for the very same reasons. Reductions 31 Zinc Reduction. ) CPB, 16(2), 217. 53 g of nitrostyrene (or equimolar amount of nitropropene) and amalgamated zinc (made from 200 g zinc powder and 20 g of HgCl2, 20 ml coned HC1 acid and 200 ml water; after a few min of agitation, decant the liquid off and use the wet zinc immediately) are suspended in 2 liters of ethanol.
Store in a closed bottle. Reductions 39 This reaction is highly exothermic, so heat is normal. , the first formula in the amphetamines chapter). Reduction with LAH and Aluminum Chloride. This gives some of the best yields possible, of all reductions known to me. It is designed to reduce phenylacetonitriles but may also be used to give high yields with reductions of nitropropenes, etc. It is used for reducing diphenylacetonitrile (see analgesics, the Amidone formula, for the synthesis of diphenylacetonitrile), to give diphenylethylamine; however, phenylacetonitrile may also be used to give phenethylamine (see precursors section to get several different formulas for phenylacetonitrile).