Aniline → N-Phenyl-9-aminophenanthrene

HRID 924548Notes

Reaction equation

HRID 924548 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:17]1([NH:16][C:2]2[C:3]3[C:8]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[CH:15]=2)=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 113099-BromophenanthreneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxide

Product 1

HCID 9943327N-Phenyl-9-aminophenanthreneYield 63%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

9-bromophenanthrene (7.00 g, 27.22 mmol), aniline (3.7 mL, 40.84 mmol), Pd2(dba)3 (499 mg, 0.544 mmol), tris-t-butylphosphine (0.123 mL, 0.544 mmol), sodium tert-butoxide (3.90 mg, 40.84 mmol) were put in a 250 mL two-neck flask and dissolved in toluene. The solution was refluxed and stirred for 12 hours. After completion of the reaction, the solution was extracted with DI water/methylenechloride and distilled under reduced pressure to remove the solvent. The resultant was columned with a solution of n-hexane and methylenechloride (3:1) and was re-crystallized in a solution of methylene chloride and petroleum ether such that the solid compound was obtained, (4.60 g, yield: 63%).

Workup

  1. temperatureThe solution was refluxed
  2. customAfter completion of the reaction
  3. extractionthe solution was extracted with DI water/methylenechloride
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customwas re-crystallized in a solution of methylene chloride and petroleum ether such that the solid compound
  7. customwas obtained

Sources & evidence

ORD record
ord-72ffdfea403a42849c0c4a9bf486cbad
Source dataset
uspto-grants-2016_03
Patent number
US09281482B2

Reaction notes

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