Aniline → 1-Phenyl-2,5-dihydro-1H-pyrrole

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To a solution of 60.0 g of the cis-2-butene derivative solution prepared in Example 1 and 250 g of toluene in a round flask reactor, 149.0 g (1.6 mol) of aniline was added dropwise with stirring for 30 min. at 50° C. After 2 hours of stirring, the crystallized solid was removed by filtration; 42.0 g of 35% HCl (aq) was added to the filtrate, and then excess benzylamine hydrochloride was removed by filtration or extraction. After the solvent was evaporated under reduced pressure, 52.2 g of 1-phenyl-3-pyrroline (yield 90.0%) was obtained.

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