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2-Phenylcinchoninic Acid absolute ether Acetic Anhydride acetyl chloride alcohol analgesics attempt to prepare B.p. Pressure Yield benzene brown oil brown solid cinchophen compound cooled crystallized cyclization dark brown dissolved distilled dropping funnel dry ether dry hydrogen chloride ester ethanol ether ether layer ether solution Ethyl 2-Phenylcinchoninate extracted with ether filtered filtrate flask equipped flask were placed Fraction friable gave glacial acetic acid grams Grignard gummy heated hydrochloric acid hydrochloride hydrogen bromide hydrogen chloride hydrolysis hydroquinoline ice bath ketone liquid melting point methacrylonitrile methanol methyl N-methylanthranilate methylaniline mixture melting point mole nitrile nitrogen one-half hour one-liter picrate platinum oxide portions of ether potassium carbonate precipitate pressure drop propionic anhydride pyridine quinoline reaction mixture recrystallization reduction residue saturated secondary amine series of reactions sodium hydroxide sodium sulfate solution was refluxed solvent stand overnight starting material synthesis tetrahydroquinoline thionyl chloride tion toluene vacuo washed water bath white solid yellow