1-p-Nitrophenyl-ethylenediaminetetracetic acid → 12-Amino-phenyl-edta

関与物質

反応手順

43 mg, 0.10 mmol of 1-(p-Nitrophenyl)-ethylenediaminetetraacetic acid was dissolved in 50 ml of aqueous NaOH (such that the final pH was 9), and 29 mg of 10% Pd/charcoal catalyst was added. The mixture was stirred gently for 5 hr in an ice bath under 1 atm of hydrogen. The catalyst was removed by filtration, and the filtrate was evaporated to dryness. In D2O, the aromatic region of the 60 MHz nmr spectrum of the 1-(p-Aminophenyl)-ethylenediaminetetraacetic acid product consisted of an aa'bb' pattern centered 7.0 ppm downfield from Me4Si. The differences in the nmr spectra of the products of Steps V and VI make it convenient to monitor the progress of the reduction by nmr. By this criterion, the reduction was quantitative. The product was stored in the dark at -15°.

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