Carbazole → 9-Acetyl-9H-carbazole

HRID 1591782Notes

Reaction equation

HRID 1591782 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-d485cc5b4b0e402f92d18dc97bf252c1
Source dataset
uspto-grants-2007_11
Patent number
US07291641B2

Reaction notes

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