Ethylenediamine → cis-Cinnamic acid

Participants

Reaction Steps

Nickel (II) acetate tetrahydrate (0.16 g, 0.00063 moles) was dissolved in ethanol (6.3 mL) and placed under hydrogen atmosphere. The green solution was stirred rapidly while sodium borohydride (0.024 g, 0.00063 moles) in ethanol (0.63 mL) was added. The deep purple solution was then treated with ethylene diamine (0.42 mL, 0.0063 moles) followed by 3-phenylpropynoic acid (0.73 g, 0.005 moles). The reaction was stirred under hydrogen for 5 hours. The hydrogen was displaced with nitrogen and the suspension was filtered through diatomaceous earth to remove the catalyst. The filtrate was concentrated in vacuo. The residue was taken up in chloroform and water, and concentrated hydrochloric acid was added to acidify the aqueous layer. The layers were separated and the acidic layer was extracted three times more with chloroform. The organic layers were combined and concentrated. The material was purified by reverse phase HPLC on a Waters Bondapak® C18 column using a gradient of 10-40% acetonitrile and 0.25% aqueous trifluoroacetic acid as the eluent to give a white solid (0.51 g).

Provenance & Evidence