Hydrochloric Acid → Indole-5-carboxaldehyde

HRID 1166734Notes

Reaction equation

HRID 1166734 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8](S(C1C=CC(C)=CC=1)(=O)=O)[CH:7]=[CH:6]2)=[O:2].[OH-].[K+].Cl>CO>[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 12013293HCID 12013293, compound

Product 1

HCID 589040Indole-5-carboxaldehydeYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-formyl-N-tosylindole (0.5 g, 1.7 mmol) was dissolved in a mixture of methanol (10 mL) containing 5% aqueous KOH solution (5 mL). The mixture was refluxed for 3 h, neutralized with 1N hydrochloric acid, and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried (MgSO4), and concentrated. The residue was purified by short column chromatography to provide 240 mg (97%) of the desired product.

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by short column chromatography

Sources & evidence

ORD record
ord-2fedcc91cf52464fa74e411a755f7e9e
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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