Water → N-[3-(3-dimethylamino-1-oxo-2-propenyl)phenyl]-methylamine

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Reaction Conditions

Reaction Steps

8.37 g (36.21 mmol) de N-(3-acetylphenyl)-2,2,2-trifluoro-acetamide were dissolved in 80 ml of N,N-dimethyl formamide. To the resultant solution 24.23 ml (181.02 mmol) of N,N-dimethylformamide dimethyl acetal were added and heated at 150° C. for 2 h. The solvent was removed by reduced pressure distillation to yield an oil which was treated with 50 ml of water and extract with 3×100 ml of dichloromethane. The organic layers were washed with 2×200 ml of a saturated solution of sodium chloride, dried over anhydrous sodium sulfate and evaporated to dryness by reduced pressure distillation. A solid was obtained, which precipitated from a mixture of ethanol-ethyl ether to give 4.1 g (yield=55%) of 3-(dimethylamino)-1-[3-(methylamino)phenyl]prop-2-en-1-one.

Provenance & Evidence