Carbazole → HCID 21476709, compound

HRID 260294Notes

Reaction equation

HRID 260294 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:14][CH2:15][CH2:16][C:17](Cl)=[O:18].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C)([O-])=O>[Cl:14][CH2:15][CH2:16][C:17]([C:3]1[CH:2]=[CH:1][C:13]2[NH:12][C:11]3[C:6]([C:5]=2[CH:4]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3)=[O:18]

Participants

5

Reactant 3

HCID 6854CarbazoleHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21476709HCID 21476709, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a 90 ml solution of 5.0 g of carbazole and 4.2 g of 3-chloropropionyl chloride in nitromethane, 4.8 g of aluminum chloride was added portionwise, followed by stirring at 45° C. for 1 hour. The reaction mixture was poured over 100 ml of ice water, and the organic layer was separated and then washed by sequential additions of a 50 ml saturated aqueous sodium hydrogen carbonate solution and 50 ml of distilled water. After the mixture was dried over anhydrous sodium sulfate, the solvent was distilled off to yield a crystalline residue. The residue was collected by filtration and dried under reduced pressure to yield 4.8 g of the title compound as a light red crystal having a melting point of 148° to 151° C.

Workup

  1. customthe organic layer was separated
  2. washwashed by sequential additions of a 50 ml saturated aqueous sodium hydrogen carbonate solution and 50 ml of distilled water
  3. dry with materialAfter the mixture was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. customto yield a crystalline residue
  6. filtrationThe residue was collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-a32129c05dd24fa8a3a5edf94d9450d3
Source dataset
uspto-grants-1996_06
Patent number
US05527800

Reaction notes

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