Aug. 5 , 1939 DEMETHYLATION OF COTININE in I.'ZVO 395 1 bath for 12 hr. The manganese dioxide was centrifuged off and the alkaline supernatant liquid extracted with ether. The aqueous layer was then evaporated to small bulk and acidified with a few drops of concentrated hydrochloric acid and extracted many times with ether (500 ml.). The dried ether extract was evaporated and the crystalline residue sublimed in v u 2 0 to yield phthalic anhydride (24.2 mg., 42%), m.p. 130 . N-Phenylphthalimide was obtained by refluxing a few mg. of the anhydride with a drop of aniline and several drops of acetic acid. CrystallizaDtion from ethanol gave fine colorless needles, map. 212 , not depressed on admixture with authentic material.Anthranilic Acid (XI).'*-The phthalic anhydride (15 mg.) was dissolved in concentrated sulfuric acid (0.2 ml.), cooled and sodium azide (30 mg.) added. The mixture was warmed at 110' on a metal-bath for 30 minutes and then allowed to cool overnight. Ice was then added and the solution brought to a p H of about 5 by the addition of SOdium hydroxide. Extraction of this solution with ether yielded anthranilic acid, purified by sublimation (10.2 mg., 73%), m.p. 145-146", not depressed on admixture with authentic material.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.