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

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A mixture 2 g (0.006 mole) of [2-[(3-nitro-2-pyridinyl)amino]phenyl]phenylmethanone, 3 g (0.019 mole) of 3-dimethylaminopropyl chloride hydrochloride, 10 ml of 50% aqueous sodium hydroxide, 5 drops tricaprylylmethyl ammonium chloride (phase transfer catalyst) and 15 ml methylene chloride was stirred and maintained at reflux for 18 hrs. Chemical ionization mass spectral analysis indicated only a trace of the starting methanone was present with good conversion to the title compound. The reaction mixture was partially neutralized with 10% hydrochloric acid. The diluted but still basic mixture was extracted with methylene chloride and the methylene chloride layer evaporated to give 1.1 g brown residue predominantly the title compound.

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