HCID 21951478, compound → HCID 21951486, compound

HRID 1760350Notes

Reaction equation

HRID 1760350 reaction equation
[N+:1]([C:4]1[CH:40]=[CH:39][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)=[CH:11][C:10]=2[P:25](=[O:38])([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:6][CH:5]=1)([O-])=O>[Pd].O1CCOCC1>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=3)=[CH:11][C:10]=2[P:25](=[O:38])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:39][CH:40]=1

Participants

4

Reactant 1

HCID 21951478HCID 21951478, compound

Product 1

HCID 21951486HCID 21951486, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Into a 250 mL Paar Hydrogenation flask was charged [2,5-bis(4-nitrophenoxy)phenyl]diphenylphosphine oxide (5.4 g, 0.0098 mol) and 1,4-dioxane (100 mL). The solution was warmed to effect dissolution with subsequent cooling to room temperature upon which 10% Pd/C (0.59 g) was added. The mixture was degassed prior to the introduction of hydrogen gas. The mixture was agitated under a hydrogen atmosphere for ˜24 hours at room temperature. After degassing the solution, the Pd/C was removed by filtration and the solution added to stirred water to afford an off white solid. The crude solid was collected via filtration, washed with water, and dried at room temperature to afford 4.1 g (76% crude yield). The solid exhibited a broad endothermic peak at 200.7° C. as determined by DSC at a heating rate of 10° C./min. Recrystallization from aqueous ethanol afforded a tan solid (3.2 g, 80% yield) exhibiting a broad endothermic peak at 204.12° C. by DSC.

Workup

  1. temperatureThe solution was warmed
  2. dissolutiondissolution
  3. additionwas added
  4. customThe mixture was degassed
  5. customAfter degassing the solution
  6. customthe Pd/C was removed by filtration
  7. additionthe solution added
  8. stirringto stirred water
  9. customto afford an off white solid
  10. filtrationThe crude solid was collected via filtration
  11. washwashed with water
  12. customdried at room temperature
  13. customto afford 4.1 g (76% crude yield)
  14. customat 200.7° C.
  15. customRecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-c97669ddf1dd4d63a1939da7437d5b52
Source dataset
uspto-grants-2005_01
Patent number
US06841652B2

Reaction notes

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