Sodium Hydroxide → [2-[[3-(Dimethylamino)propyl](3-nitro-2-pyridinyl)amino]phenyl]phenylmethanone

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A mixture of 3.6 g (0.01 mole) of [2-[(3-nitro-2-pyridinyl)amino]phenyl]phenylmethanone hydrochloride, 4.7 g (0.03 mole) of 3-dimethylaminopropyl chloride, 0.1 g of tricaprylyl ammonium chloride, 16 g (0.20 moles) of 50% aqueous sodium hydroxide, 25 ml methylene chloride, and 5 ml water was refluxed for 27 hrs. Chemical ionization mass spectroscopy analysis indicated the product was mainly the title compound. The mixture was cooled and diluted with methylenechloride-water mixture. The aqueous layer was extracted twice with methylene chloride. The combined methylene chloride layers were washed with aqueous sodium chloride solution, dried, treated with charcoal, filtered and evaporated to give 3.3 g black material (81.5%) which was predominantly the title compound as indicated by thin-layer chromatography and chemical ionization mass spectroscopy analysis of the chromatographed material, i.e. m/e=405.

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