Water → 9-(4-Nitrophenyl)-9H-carbazole

HRID 703054Notes

Reaction equation

HRID 703054 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[CH:16][CH:17]=1)([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6854CarbazoleHCID 74741-Chloro-4-nitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 6256499-(4-Nitrophenyl)-9H-carbazole

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 334.4 (2 mol) of carbazole, 472.8 g of p-chloro-nitrobenzene (3 mol) and 691 g (5 mol) of anhydrous potassium carbonate were stirred in 1500 ml of dimethylacetamide for 13 h at reflex temperature. The reaction mixture was then poured into 7 of water and the precipitate separated by suction filtering. Said precipitate was stirred in 4 of water and neutralized with 1 N hydrochloric acid, whereupon the precipitate was filtered again. After drying the solid product was recrystallized from a mixture of tetrahydrofuran and methanol and the yellow product obtained was dried. Yield: 465 g. Melting point: 211° C.

Workup

  1. customthe precipitate separated by suction
  2. filtrationfiltering
  3. filtrationwas filtered again
  4. customAfter drying the solid product
  5. customwas recrystallized from a mixture of tetrahydrofuran and methanol
  6. customthe yellow product obtained
  7. customwas dried

Sources & evidence

ORD record
ord-e5f5c82f4b05485fadcaed1aacdeb0ea
Source dataset
uspto-grants-1991_01
Patent number
US04981768

Reaction notes

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