HCID 21951478, compound → HCID 21951486, compound

HRID 968174Notes

Reaction equation

HRID 968174 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, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Into a 250 mL Parr hydrogenation flask were 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). Recrystallization from aqueous ethanol afforded [2,5-bis(4-aminophenoxy)phenyl]diphenylphosphine oxide as a tan solid (3.2 g, 80% recovery), m.p. 205-208° C. Anal. Calcd. for C30H25N2O3P: C, 73.16%; H, 5.12%; N, 5.69%; P, 6.29%. Found: C, 72.87%; H, 5.08%; N, 5.78%; P, 5.64%.

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. customRecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-c24ab85e09dd4b4c8d810ad1cf76b3f3
Source dataset
uspto-grants-2005_10
Patent number
US06958192B2

Reaction notes

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