Sodium Carbonate → N-(2-diethylaminoethyl)-N-ethyl-2-(8-trifluoromethyl-4-quinolylamino)benzamide

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Reaction Steps

12.1 Grams (0.03 mole) of 2-(8-trifluoromethyl-4-quinolylamino)benzoic acid hydrochloride dihydrate were refluxed in 80 milliliters of thionyl chloride for half an hour. A yellow solid precipitated. The thionyl chloride was evaporated off and 50 milliliters of benzene were added and evaporated. The resulting acid chloride hydrochloride was added in portions with stirring to a cooled mixture of 4.32 grams (0.03 mole) of N,N,N'-triethylethylenediamine in 80 milliliters of chloroform and 31.8 grams (0.3 mole) of sodium carbonate in 100 milliliters of water. The mixture was stirred for one hour, and allowed to stand overnight. The chloroform layer was separated and dried and the chloroform evaporated to give an oil, which could not be solidified. The oil was dissolved in ether and purified by chromatography on an alumina (type H) column. Elution with ether/chloroform (50:50) gave a pale yellow oil which was kept under vacuum for four days when it gradually solidified to give 6.35 grams (46% yield) of title compound of melting point 112°-113° C.

Provenance & Evidence