Carbazole → HCID 45071617, compound

HRID 513316Notes

Reaction equation

HRID 513316 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.[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1Br.C([O-])([O-])=O.[K+].[K+].[O-]S([O-])(=O)=O.[Na+].[Na+].[N+](C1C=CC=CC=1)([O-])=O>>[CH:10]1[C:11]2[N:12]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16]([O:15][CH3:14])=[O:24])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 5

HCID 6854CarbazoleHCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 11894Methyl 2-bromobenzoateHCID 24436Sodium Sulfate

Product 1

HCID 45071617HCID 45071617, compoundYield 79.6%

Procedure

A 1 L round bottom flask was charged with carbazole (8.36 g, 50 mmol), methyl-2-bromobenzoate (15 g, 75 mmol), K2CO3 (7 g, 50 mmol), Na2SO4 (7.1 g, 50 mmol), Cu powder (0.3 g, 5 mmol), and nitrobenzene, and the mixture was reacted at 190° C. for 24 hours. After the reaction was completed, the resultant product was extracted with methylene chloride and water. The organic layer was dried with MgSO4, and purified by silica gel column (ethyl acetate:hexane=1:5) to give 12 g of a product (79.6%).

Workup

  1. customthe mixture was reacted at 190° C. for 24 hours
  2. extractionthe resultant product was extracted with methylene chloride and water
  3. dry with materialThe organic layer was dried with MgSO4
  4. custompurified by silica gel column (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-3510ae02d4484b18852d5e99aa7521c9
Source dataset
uspto-grants-2015_08
Patent number
US09102616B2

Reaction notes

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