Methanol → 9-Ethyl-9H-carbazole-3-carboxylic acid

HRID 50609

Reaction equation

HRID 50609 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].[Mn]([O-])(=O)(=O)=[O:19].[K+].CO>CC(C)=O>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16]([OH:19])=[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 3

HCID 887MethanolHCID 820559-ethyl-9H-carbazole-3-carbaldehydeHCID 516875Potassium Permanganate

Product 1

HCID 49128699-Ethyl-9H-carbazole-3-carboxylic acidYield 61.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

50 g of N-ethylcarbazole-3-carboxaldehyde was dissolved in 1 L of acetone, and the solution was added with 70.6 g of potassium permanganate under ice cooling, stirred for 3 hours, then added with 100 mL of methanol and filtered. The filtrate was evaporated under reduced pressure, and the residue was dissolved in aqueous sodium hydrogencarbonate. Then, the solution was made acidic by adding concentrated hydrochloric acid, and the deposited precipitates were collected to obtain 33 g of N-ethylcarbazole-3-carboxylic acid.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in aqueous sodium hydrogencarbonate
  4. additionby adding concentrated hydrochloric acid
  5. customthe deposited precipitates
  6. customwere collected

Sources & evidence

ORD record
ord-cd235a0093da40bfaf22543d6aff285a
Source dataset
uspto-grants-2004_03
Patent number
US06713473B1

Linked notes

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