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1,10-Phenanthroline → [1,1'-Biphenyl]-4-amine, N,N-bis(3,4-dimethylphenyl)-

HRID 1300
Notes
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Reaction equation

HRID 1300 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([CH3:17])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].I[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[OH-].[K+]>C1(C)C=CC=CC=1>[CH3:17][C:12]1[CH:11]=[C:10]([N:9]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=2)[C:28]2[CH:29]=[CH:30][C:25]([C:22]3[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=3)=[CH:26][CH:27]=2)[CH:15]=[CH:14][C:13]=1[CH3:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 13181,10-PhenanthrolineHCID 14797Potassium HydroxideHCID 153224-IodobiphenylHCID 614511Bis(3,4-dimethylphenyl)amine

Product 1

HCID 10595766[1,1'-Biphenyl]-4-amine, N,N-bis(3,4-dimethylphenyl)-

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Conditions

Temperature
120 °C

Procedure

In a 500 milliliter round bottomed flask equipped with mechanical stirrer and fitted with a Dean-Stark trap under a reflux condenser were placed 12.39 grams (0.055 mole) of bis(3,4-dimethylphenyl)amine, 14 grams (0.050 mole) of 4-iodobiphenyl, 0.25 gram (0.0025 mole) of cuprous chloride, 0.45 gram (0,0025 mole) of 1,10-phenanthroline, 22.44 grams (0.4 mole) of flake potassium hydroxide and 20 milliliters of toluene solvent. The reaction was heated quickly to a reflux temperature of 120° C. and maintained at this temperature for 4 hours after which time chromatographic analysis revealed the reaction to be complete. The reaction was cooled to room temperature, about 25° C., and partitioned between 200 milliliters of toluene and 150 milliliters of deionized water. The resulting organic layer was separated and water removed by azeotropic distillation of the solvent under a Dean-Stark trap. The product was decolorized by slurry treating the toluene solution with 10 grams of Filtrol-24™, an acid washed clay, and 10 grams of Alcoa CG-20 alumina. After 3 hours stirring at reflux, the solution was hot filtered to remove the clay and alumina, and cooled to room temperature. Evaporation of the solvent and recrystallization from octane provided the above product compound in a yield of 10.2 grams (76 percent) and which product melted at 113.8° C. This product of N,N-bis(3,4-dimethylphenyl)-4-biphenylamine was suitable for further purification by conventional means to afford electronic grade, about 99 percent pure, product. The above total reaction time was an accelerated 4 hours.

Workup

  1. customIn a 500 milliliter round bottomed flask equipped with mechanical stirrer
  2. customfitted with a Dean-Stark trap under a reflux condenser
  3. temperaturemaintained at this temperature for 4 hours after which time chromatographic analysis
  4. customthe reaction
  5. temperatureThe reaction was cooled to room temperature, about 25° C.
  6. custompartitioned between 200 milliliters of toluene and 150 milliliters of deionized water
  7. customThe resulting organic layer was separated
  8. customwater removed by azeotropic distillation of the solvent under a Dean-Stark trap
  9. additiontreating the toluene solution with 10 grams of Filtrol-24™
  10. washan acid washed clay, and 10 grams of Alcoa CG-20 alumina
  11. temperatureat reflux
  12. filtrationthe solution was hot filtered
  13. customto remove the clay and alumina
  14. temperaturecooled to room temperature
  15. customEvaporation of the solvent and recrystallization from octane

Sources & evidence

ORD record
ord-84448ea235a5434095bfa277b099b79d
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723669

Reaction notes

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