1,2-Dichlorobenzene → 9H-carbazole-2-carbonitrile

HRID 539472Notes

Reaction equation

HRID 539472 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O-])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC1C=CC=CC=1Cl>C1(C)C=CC=CC=1>[CH:9]1[C:4]2[NH:1][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:5]=2[CH:6]=[CH:7][C:8]=1[C:10]#[N:11]

Participants

5

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 11776TriphenylphosphineHCID 104893112-Nitrobiphenyl-4-carbonitrile

Product 1

HCID 117356699H-carbazole-2-carbonitrileYield 36.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-nitro-[1,1′-biphenyl]-4-carbonitrile (8.87 g, 39.6 mmol) and triphenylphosphine (25.9 g, 99 mmol) were charged into the reaction flask with 90 mL of 1,2-dichlorobenzene. This mixture was stirred and heated at reflux for 24 hours. The reaction mixture was diluted with 50 mL of toluene then was loaded directly onto a neutral alumina column. The column was eluted with 100% toluene followed by 5% ethyl acetate/toluene (v/v). The product fractions were combined and concentrated under vacuum. This product was then passed through a silica gel column eluting first with 80-99% DCM/hexanes then 5% ethyl acetate/DCM. The product, 9H-carbazole-2-carbonitrile (2.75 g, 14.31 mmol, 36.2% yield) was isolated as a light tan solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. washThe column was eluted with 100% toluene
  4. concentrationconcentrated under vacuum
  5. washeluting first with 80-99% DCM/hexanes

Sources & evidence

ORD record
ord-8125d0b16418464a9e8a346f2f880c90
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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