Ammonium formate → HCID 54396539, compound

Participants

Reaction Steps

2,9-Bis[N,N-di(ethoxycarbonylmethyl)aminomethyl]-5-nitro-1,10-phenanthroline (3.37 g, 5.4 mmol) was dissolved in a solution of 100 mL tetrahydrofuran and 200 mL absolute ethanol. A solution of 6.8 g (108 mmol) of ammonium formate in 22 mL of distilled H2O was added, followed by 5.72 g of palladium on carbon (10%) (50% wet with water for safety). The reaction was stoppered with a gas bubbler, stirred at room temperature for 30 minutes, and then filtered through a diatomaceous earth filter pad. The solvents were then removed on a rotary evaporator. The residue was dissolved in 300 mL of dichloromethane which was then extracted with 300 mL of distilled water. The organic phase was extracted with 300 mL of saturated sodium chloride, dried with a mixture of Celite diatomaceous earth and sodium sulfate, filtered, and then concentrated under high vacuum to a dark amber oil which weighed 2.90 g. The oil was treated with 9.0 mL of propionitrile to induce the crystallization of a yellow solid. The solid was filtered, washed with 13 mL of propionitrile, 15 mL of hexanes, and then air dried to a constant weight of 1.04 g (32%); mp 137°-139° C. FDMS (m/e) 598 MH+, 597 M. Anal. calcd. for C30H39N5O9.H2O: C, 58.52; H, 6.71; N, 11.38. Found: C, 58.28; H, 6.55; N, 11.53. The NMR and IR spectra were consistent with the assigned structure.

Provenance & Evidence