Acetonitrile → 9-Allylcarbazole

HRID 36382

Reaction equation

HRID 36382 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.[CH2:14](Br)[CH:15]=[CH2:16].C(=O)([O-])[O-].[K+].[K+].C(#N)C>ClCCl>[CH2:16]([N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH:15]=[CH2:14]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6854CarbazoleHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 30903939-Allylcarbazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 500-mL, three-necked, round-bottomed flask, equipped with a magnetic stirrer, a thermometer, and a condenser connected to a nitrogen bubbler, were placed carbazole (8.4 g, 50 mmole), allyl bromide (10 mL, 115 mmole), powdered anhydrous potassium carbonate (41 g, 300 mmole), and anhydrous acetonitrile (300 mL). The resultant mixture was stirred and heated under reflux with a heating mantle for 18 hours. Dichloromethane (300 mL) was then added, and the mixture was filtered through a pad of Celite. The clear filtrate was evaporated, and the residue was recrystallized from methanol to yield the desired product as amber-colored crystals. The product had melting point 56°-57° C., and sublimation (100° C./0.1 mm Hg) yielded white crystals (8.65 g, 83%), melting point 57°-58° C. The proton NMR spectrum in carbon tetrachloride was

Workup

  1. customInto a 500-mL, three-necked, round-bottomed flask, equipped with a magnetic stirrer
  2. temperatureheated
  3. temperatureunder reflux with a heating mantle for 18 hours
  4. filtrationthe mixture was filtered through a pad of Celite
  5. customThe clear filtrate was evaporated
  6. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-2db01ce7b32a46519cdefc6ef82ad7c5
Source dataset
uspto-grants-1995_05
Patent number
US05414069

Linked notes

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