Carbazole → 9-Acetyl-9H-carbazole

HRID 2421279Notes

Reaction equation

HRID 2421279 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(O)(=O)(=O)=O.[C:19](OC(=O)C)(=[O:21])[CH3:20]>>[C:19]([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)(=[O:21])[CH3:20]

Participants

4

Reactant 3

HCID 6854CarbazoleHCID 7918Acetic AnhydrideHCID 24247Perchloric Acid

Product 1

HCID 958379-Acetyl-9H-carbazoleYield 90%

Procedure

This compound is obtained according to Tetrahedron (1980), 36, 3017-3019. The carbazole (10 g; 60 mmol) is suspended in 150 ml of acetic anhydride. 70% perchloric acid (0.5 ml) is added. After stirring for 30 minutes at ambient temperature, the mixture is poured into ice and the precipitate formed is filtered. After drying under vacuum, redissolving in dichloromethane and treatment with bone charcoal, the suspension is filtered on celite, the solvents are evaporated off and the product recrystallized from heptane. 12 g of brown crystals (yield of 90%) is obtained in this way. Melting point: 70-71° C. (literature: 72-74° C.).

Workup

  1. customThis compound is obtained
  2. additionthe mixture is poured into ice
  3. customthe precipitate formed
  4. filtrationis filtered
  5. customAfter drying under vacuum
  6. dissolutionredissolving in dichloromethane
  7. filtrationtreatment with bone charcoal, the suspension is filtered on celite
  8. customthe solvents are evaporated off
  9. customthe product recrystallized from heptane

Sources & evidence

ORD record
ord-67cb795502e949b281fc0fa3f5becdf4
Source dataset
uspto-grants-2011_06
Patent number
US07956075B2

Reaction notes

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