9-ethyl-9H-carbazole-3-carbaldehyde → 9-Ethyl-9H-carbazole-3-carboxylic acid

HRID 2184932

Reaction equation

HRID 2184932 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH:16]=[O:17])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[O-:18][Mn](=O)(=O)=O.[K+]>CC(C)=O.O>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16]([OH:18])=[O:17])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

5

Reactant 2

HCID 820559-ethyl-9H-carbazole-3-carbaldehydeHCID 516875Potassium Permanganate

Product 1

HCID 49128699-Ethyl-9H-carbazole-3-carboxylic acidYield 76%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 9-Ethyl-9H-carbazole-3-carbaldehyde (Aldrich, 5.0 g, 22.39 mmol) in acetone (100 ml) at 70° C. under nitrogen was added dropwise a solution of KMnO4 (4.74 g, 30.00 mmol) in H2O (100 ml) slowly over 1 hour. When the reaction was complete the reaction mixture was filtered through celite, the celite pad washed with H2O/acetone, and the filtrate washed with ether. The aqueous layer was then acidified to pH 2 with aqueous HCl, and the white precipitate filtered and dried under vacuum to afford the desired product (4.05 g, 76% yield). MS m/z @ 240 (m+1).

Workup

  1. filtrationwas filtered through celite
  2. washthe celite pad washed with H2O/acetone
  3. washthe filtrate washed with ether
  4. filtrationthe white precipitate filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d3f3dce7920944ad8dd8114c4436535d
Source dataset
uspto-grants-2002_06
Patent number
US06399631B1

Linked notes

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