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

HRID 1361741Notes

Reaction equation

HRID 1361741 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, 340 mg (0.6 mmol) of bis(dibenzylideneacetone)palladium(0), 1.6 g (3.0 mmol) of 1,1-bis(diphenylphosphino)ferrocene, and 13 g (180 mmol) of sodium-tert-butoxide, and the atmosphere in the flask was substituted by nitrogen. Thereafter, 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. After the reaction was completed, about 500 mL of hot toluene was added to the reacted mixture, and this mixture was filtered through Florisil, alumina, and celite. An oily substance was obtained by concentration of the filtrate, and hexane and ethyl acetate were added to the substance, which was followed by irradiation with ultrasound. A solid precipitated was collected by suction filtration and dried to give 15 g (75% yield) of N-phenyl-(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA) as cream colored powder. By a nuclear magnetic resonance measurement (NMR), it was confirmed that this compound was N,9-diphenyl-9H-carbazol-3-amine (abbreviation: PCA).

Workup

  1. temperatureThis mixture was heated
  2. filtrationthis mixture was filtered through Florisil, alumina, and celite
  3. customAn oily 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 ultrasound
  6. customA solid precipitated
  7. filtrationwas collected by suction filtration
  8. customdried

Sources & evidence

ORD record
ord-f5f862fc256d4edc8fcdc94c4fb81d6f
Source dataset
uspto-grants-2011_02
Patent number
US07880019B2

Reaction notes

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