Ammonium formate → HCID 54396539, compound

HRID 725692Notes

Reaction equation

HRID 725692 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]([CH2:14][C:15]1[CH:28]=[CH:27][C:26]2[C:17](=[C:18]3[C:23](=[CH:24][C:25]=2[N+:29]([O-])=O)[CH:22]=[CH:21][C:20]([CH2:32][N:33]([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[N:19]3)[N:16]=1)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])[CH3:2].C([O-])=O.[NH4+]>O1CCCC1.C(O)C.O.[Pd]>[NH2:29][C:25]1[CH:24]=[C:23]2[C:18]([N:19]=[C:20]([CH2:32][N:33]([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:21]=[CH:22]2)=[C:17]2[C:26]=1[CH:27]=[CH:28][C:15]([CH2:14][N:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[N:16]2

Participants

7

Reactant 2

HCID 2723923Ammonium formateHCID 53941755HCID 53941755, compound

Product 1

HCID 54396539HCID 54396539, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. filtrationfiltered through a diatomaceous earth
  2. filtrationfilter pad
  3. customThe solvents were then removed on a rotary evaporator
  4. dissolutionThe residue was dissolved in 300 mL of dichloromethane which
  5. extractionwas then extracted with 300 mL of distilled water
  6. extractionThe organic phase was extracted with 300 mL of saturated sodium chloride
  7. dry with materialdried with a mixture of Celite diatomaceous earth and sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under high vacuum to a dark amber oil which
  10. additionThe oil was treated with 9.0 mL of propionitrile
  11. customthe crystallization of a yellow solid
  12. filtrationThe solid was filtered
  13. washwashed with 13 mL of propionitrile, 15 mL of hexanes
  14. customair dried to a constant weight of 1.04 g (32%)

Sources & evidence

ORD record
ord-4cedd0950bcc482aae2608b4435c108d
Source dataset
uspto-grants-1998_01
Patent number
US05707603

Reaction notes

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