Carbazole → 9-Acetyl-9H-carbazole

HRID 2065978Notes

Reaction equation

HRID 2065978 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-1d49a6a6b4a54eb18b497d7787d8cebc
Source dataset
uspto-grants-2012_10
Patent number
US08288560B2

Reaction notes

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