Ammonium formate → HCID 54396539, compound

HRID 2380415Notes

Reaction equation

HRID 2380415 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 by 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 then extracted with 300 mL of saturated sodium chloride, then dried with a mixture of Celite diatomaceous earth and sodium sulfate, filtered, and concentrated under high vacuum to a dark amber oil which weighed 2.90 g. The oil was treated with 9.0 mL of propionitrile, which resulted in the crystallization of a yellow solid. The solid was filtered, and washed with 13 mL of propionitrile, and finally washed with 15 mL of hexanes, and 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 C30H39N5O 9 ·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 by a rotary evaporator
  4. dissolutionThe residue was dissolved in 300 mL of dichloromethane
  5. extractionwhich was then extracted with 300 mL of distilled water
  6. extractionThe organic phase was then 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, which
  11. customresulted in the crystallization of a yellow solid
  12. filtrationThe solid was filtered
  13. washwashed with 13 mL of propionitrile
  14. washfinally washed with 15 mL of hexanes, and air
  15. customdried to a constant weight of 1.04 g (32%) mp 137°-139° C

Sources & evidence

ORD record
ord-dbfabf2dfcbf40ab9e7f5deb445ece47
Source dataset
uspto-grants-1994_11
Patent number
US05367080

Reaction notes

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