Bis(2,4-dinitrophenyl) ether → HCID 15312385, compound

HRID 2254835Notes

Reaction equation

HRID 2254835 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:15]=1[N+:23]([O-])=O)([O-])=O.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:23][C:15]1[CH:16]=[C:17]([NH2:20])[CH:18]=[CH:19][C:14]=1[O:13][C:5]1[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=1[NH2:1]

Participants

5

Reactant 2

HCID 95146Bis(2,4-dinitrophenyl) etherHCID 178418361HCID 178418361, compound

Product 1

HCID 15312385HCID 15312385, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

The dinitro compound obtained from Example 7 (22.1 g, 0.035 mole) was mixed with 10% Pd/C (2.2 g) in ethyl acetate/ethanol (6/4 by volume, 88 g) solvent. Hydrogenation was carried out with 50-60 psi of hydrogen pressure at ambient temperature for about 6 hrs. After reaction, the solution was filtered to remove the metal residue and the solvent was removed in vacuo. The final diamino product was purified by distillation, 4.75 g of (24% yield) clear, viscous liquid was obtained. Bp. 120° C./0.02 mm. H1NMR (CDCl3): δ7.61 (d, J=8.0 Hz, 1H), 6.08 (d, J=2.0 Hz, 1H), 6.02 (dd, J=2 Hz, 8 Hz, 1H), 4.11 (t, J=13.5 Hz, 2H), 3.55 (s, br, 4H, --NH2); F19NMR (CDCl3): -71.3 (m, 2F), - 77.5 (m, 1F), -80.2 (m, 3F), -82.3 to -86.0 (m, 4F), -124.0 (m, 2F), -146.2 (m, 1F).

Workup

  1. customAfter reaction
  2. filtrationthe solution was filtered
  3. customto remove the metal residue
  4. customthe solvent was removed in vacuo
  5. distillationThe final diamino product was purified by distillation, 4.75 g of (24% yield) clear
  6. customviscous liquid was obtained

Sources & evidence

ORD record
ord-7ba4ed6ea3584f7dbe1f120d466df47b
Source dataset
uspto-grants-1993_08
Patent number
US05237026

Reaction notes

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