Water → 2-Cyclopropylethynylphenylamine

Participants

Reaction Steps

0.26 g of copper(I) iodide, 0.30 g of bis(triphenylphosphine)palladium(II) dichloride and then 0.78 ml of cyclopropylacetylene are successively added to a solution of 1.0 g of 2-iodoaniline in 5 ml of triethylamine under argon. The reaction mixture is stirred at ambient temperature for 30 minutes, and then 1 ml of N,N-dimethylformamide is added. The reaction mixture is stirred at ambient temperature for 30 minutes, then 1 ml of N,N-dimethylformamide is again added. The reaction mixture is stirred at ambient temperature for 15 hours, and is then poured into 100 ml of water. After the addition of 50 ml of ethyl acetate, the mixture is filtered through Celite®, and then separated by settling out. The organic phase is separated and the aqueous phase is extracted with 3×40 ml of ethyl acetate. The organic phases are combined, washed with 2×40 ml of water, dried over anhydrous magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. The residue is purified on a 50 g column of 20-45 μm silica, elution being carried out with an 80/20 v/v dichloromethane/cyclohexane mixture. 0.42 g of 2-cyclopropylethynylphenylamine is thus obtained in the form of a brown oil which is used directly in the next step.

Provenance & Evidence