The Preparation of Some Alkyl Substituted Phenylacetonitriles in Liquid Ammonia

Abstract

Recent work in these laboratories with phenylacetonitrile, sodium and alkyl halides in liquid ammonia suggested that the reactions would be of value in synthesizing an homologous series of nitriles from which the corresponding acids could be prepared by hydrolysis. It was desired to obtain these acids in order to determine their relative bactericidal values, work to be reported elsewhere.Sodium ethylate,1 sodium hydroxide,2 sodamide,3 and sodium4 have been used to prepare the alkali salt of phenylacetonitrile as a preliminary step in the formation of substituted nitriles. Phenylacetonitrile in excess, methyl alcohol, toluene and anhydrous ether have been used as reacting media. Attempts by Bodroux and Taboury to prepare di-alkyl derivatives by treating the parent nitrile with two moles of sodamide and alkyl

Reactions of Solutions of Metals in Liquid Ammonia.

“…Magnesium likewise dissolves to a slight extent to give a pale blue solution. 3 While no other metals are definitely known to be soluble in liquid ammonia, it may be argued on the basis of certain chemical reactions that a few metals (beryllium (15), zinc (86), aluminum (6), gallium, lanthanum, cerium (10), and manganese (8)) also are soluble to a very slight extent. The tetrasubstituted ammonium radicals, whose behavior closely resembles that of the alkali metals, impart a blue color to their liquid ammonia solutions (90,173,302,332,333).…”

POTENTIAL ANALGESICS AND ANTISPASMODICS. I. THE SYNTHESIS OF OPEN-CHAIN ANALOGS OF DEMEROL1

“…6 Microanalyses by Oakwold Laboratories, Fairfax, Virginia. = Baldinger and Nieuwland (14) reported n2" 1.5077, d® 0.9717. d Hastings and Cloke (15) gave ra?,°1.5225, df 1.0784.…”

Marked differences between the sodium-ammonia and calcium-ammonia reduction of nitriles

“…The relative rates of bond breaking of the two carbon-nitrogen bonds in the thermal decomposition of unsymmetrical azo compounds has been investigated recently. 2 This and other studies have resulted in the modification of old and development of new synthetic procedures for the preparation of the requisite unsymmetrical azo compounds.8…”