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

HRID 2369622Notes

Reaction equation

HRID 2369622 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

After putting 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 into a three-neck flask and replacing the air in the flask with nitrogen, 110 mL of anhydrous xylene and 7.0 g (75 mmol) of aniline were added. This was stirred for 7.5 hours while heating at 90° C. in a nitrogen atmosphere. After the reaction, about 500 mL of hot toluene was added to the suspension and the mixture was filtered through florisil, alumina, and Celite®. The obtained filtrate was concentrated and hexane-ethyl acetate was added thereto, and then the mixture was irradiated with ultrasonic waves. The obtained suspension was filtered and the residue was dried, thereby obtaining 15 g (yield: 75%) of 3-(N-phenylamino)-9-phenylcarbazole (abbr.: PCA) as a cream-colored powder.

Workup

  1. additionwere added
  2. additionwas added to the suspension
  3. filtrationthe mixture was filtered through florisil, alumina, and Celite®
  4. concentrationThe obtained filtrate was concentrated
  5. additionhexane-ethyl acetate was added
  6. customthe mixture was irradiated with ultrasonic waves
  7. filtrationThe obtained suspension was filtered
  8. customthe residue was dried

Sources & evidence

ORD record
ord-8ce7b01e8e5d43aaa298cb6f58658d95
Source dataset
uspto-grants-2014_04
Patent number
US08704242B2

Reaction notes

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