Ammonia → 2-Phenyl-2-[4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)-phenoxy]-propionitrile

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Reaction Steps

At -40°, 50 mg. of iron (III) nitrate and then, under agitation, 2.3 g. of Na are dissolved in 100 ml. of liquid ammonia. After two hours of agitation, 3.54 g. of 2-phenyl-2-[4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)-phenoxy]-acetonitrile is added thereto, the mixture stirred for 30 minutes, and then 19.2 ml. of dimethyl sulfate is added dropwise within one hour. The mixture is further agitated overnight at -35° and then combined dropwise with another 10 ml. of dimethyl sulfate. After the ammonia has been evaporated, the residue is combined with water and extracted with ether. The crude 2-phenyl-2-[4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)-phenoxy]-propionitrile obtained after the evaporation of the ether is refluxed for 40 hours with 3 g. of KOH in 30 ml. of ethanol and 3 ml. of water. The mixture is concentrated by evaporation, mixed with water, extracted with ether, hydrochloric acid is added to pH 5, and the acid Ih is thus produced.

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