Vol. 01 anhydride dissolved in 200 cc. of neutral alcohol and titrated with 0.1 JV sodium hydroxide solution. To test the purity of the acid it was recovered and converted into phthalic anhydride. The quantitative isolation of the anhydride in this way was tested with a weighed sample which was converted into the salt, liberated and sublimed, and titrated. The recovery was 95.7%. In a second test a mixture of 1 g. each of the three phthalic acids gave a recovery of o-phthalic acid of 97%.We were unable to find a quantitative method for the separation of isophthalic and terephthalic acids. As a consequent*, the percentage of m-xylenes in the mixtures analyzed was considered to be the difference between the weights of the mixed xylenes and the sum of the ortho and para isomers. In several experiments the weight of wj-xylene was calculated from the weights of the pxylene and of the isophthalic and terephthalic acids obtained. The result checked within less than 1% the value obtained.
Rings by the Dienyne Double Addition Reaction 1311 bath at 140°for eight hours. The product was isolated as the free base by crystallization from 50% ethanol and water; yield, 2.0 g. (80%).Other Heterocyclic Substituted Aminoquinaldines.-4-Chloro-6-methoxyquinaldine (0.02 mole) was mixed well with 0.022 mole of the desired heterocyclic amine, i. e., 8aminoquinoline, 8-amino-6-methoxyquinoline, thionine (0.011 mole), and 5-aminoindazole. The reaction mixture in each case was heated in an oil-bath at 160-1750 for three hours. The products were isolated and purified by washing the residues with 5% sodium hydroxide then numerous crystallizations from 90% ethanol; yields, approximately 60 to 70%. Summary A. relatively simple and economical process for the preparation of basically substituted propylamines has been reported.4-Chloro-6-methoxyquinaldine has been condensed with a few basically substituted aliphatic amines and several heterocyclic amines to give the corresponding 4-substituted quinaldines.
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