Aniline → N,9-Diphenyl-9H-carbazol-3-amine

HRID 2063183Notes

Reaction equation

HRID 2063183 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.CC(C)([O-])C.[Na+].C1(C)C(C)=CC=CC=1.[NH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=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].[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2].C1(C)C=CC=CC=1>[C:36]1([NH:35][C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:7]4[C:12]([C:13]=3[CH:14]=2)=[CH:11][CH:10]=[CH:9][CH:8]=4)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

8

Reactant 4

HCID 6115AnilineHCID 7237O-XyleneHCID 189426243-Bromo-9-phenylcarbazoleHCID 23676156Sodium t-butoxide

Product 1

HCID 59815954N,9-Diphenyl-9H-carbazol-3-amineYield 75%

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 152416121,1`-Bis(diphenylphosphino)ferroceneCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Into a 500 mL three-neck flask were added 19 g (60 mmol) of 3-bromo-9-phenylcarbazole, 0.34 g (0.60 mmol) of bis(dibenzylideneacetone)palladium(0), 1.6 g (3.0 mmol) of 1,1-bis(diphenylphosphino)ferrocene, and 13 g (0.18 mol) of sodium tert-butoxide, and the atmosphere in the flask was substituted by nitrogen. Then, 110 mL of dehydrated xylene and 7.0 g (75 mmol) of aniline were added to the mixture. This mixture was heated and stirred at 90° C. for 7.5 hours-under nitrogen gas flow. After the reaction was completed, about 500 mL of hot toluene was added to the reacted mixture, and this mixture was filtered through Florisil (manufactured by Floridin Company), alumina, and Celite (manufactured by Celite Co., Ltd.). A solid substance was obtained by concentration of the filtrate, and hexane and ethyl acetate were added to the substance, which was followed by irradiation with ultrasonic waves, so that a solid substance was precipitated. The solid substance was collected by suction filtration and dried to produce 15 g (75% yield) of N-phenyl-(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA) as milky-white powder. By a nuclear magnetic resonance measurement (NMR), this compound was proved to be N-phenyl-(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA).

Workup

  1. temperatureThis mixture was heated
  2. filtrationthis mixture was filtered through Florisil (manufactured by Floridin Company), alumina, and Celite (manufactured by Celite Co., Ltd.)
  3. customA solid substance was obtained by concentration of the filtrate, and hexane and ethyl acetate
  4. additionwere added to the substance, which
  5. customwas followed by irradiation with ultrasonic waves, so that a solid substance
  6. customwas precipitated
  7. filtrationThe solid substance was collected by suction filtration
  8. customdried

Sources & evidence

ORD record
ord-d41ec567655442879fa1068549a21812
Source dataset
uspto-grants-2012_10
Patent number
US08288012B2

Reaction notes

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