4-Aminobiphenyl → N,N-Bis(4-methylphenyl)[1,1'-biphenyl]-4-amine

HRID 1708845Notes

Reaction equation

HRID 1708845 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1>[Cu]>[C:5]1([CH3:8])[CH:6]=[CH:7][C:2]([N:15]([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)[C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][CH:21]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 71024-AminobiphenylHCID 11430Potassium CarbonateHCID 122074-Iodotoluene

Product 1

HCID 15219415N,N-Bis(4-methylphenyl)[1,1'-biphenyl]-4-amine

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
220 °C

Procedure

A mixture of 65.4 grams of p-iodotoluene, 11.3 grams of copper bronze powder and 55.3 grams of potassium carbonate in 150 milliliters of Soltrol 220 was mechanically stirred in a 250 milliliter round-bottomed flask fitted with a reflux condenser. The mixture was first heated to 160° C. with a heating mantle before 16.92 grams of 4-aminobiphenyl was added. After the addition, the reaction mixture was heated under reflux at 220° C. for five hours. After cooling, the reaction mixture was filtered, and the resulting filter cake was washed with 50 milliliters of heptane. The filtrate was distilled under reduced pressure to remove Soltrol 220. The resulting solid residue was purified by column chromatography on silica gel to afford a white solid. Further purification by recrystallization from isopropanol yielded 16.2 grams of analytically pure bis(p-tolyl)-4-biphenylylamine, melting point, 94° to 95° C.

Workup

  1. customfitted with a reflux condenser
  2. additionwas added
  3. additionAfter the addition
  4. temperaturethe reaction mixture was heated
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture was filtered
  7. filtrationthe resulting filter cake
  8. washwas washed with 50 milliliters of heptane
  9. distillationThe filtrate was distilled under reduced pressure
  10. customto remove Soltrol 220
  11. customThe resulting solid residue was purified by column chromatography on silica gel
  12. customto afford a white solid
  13. customFurther purification
  14. customby recrystallization from isopropanol

Sources & evidence

ORD record
ord-4e2010b60a804b1b9660448deda5e9ef
Source dataset
uspto-grants-1990_08
Patent number
US04946754

Reaction notes

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