Sodium Hydroxide → 7-Chloro-1H-indole-2-carboxylic acid

HRID 1067764Notes

Reaction equation

HRID 1067764 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13]CC)=[O:12])=[CH:7]2.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13166917ethyl 7-chloro-1H-indole-2-carboxylate

Product 1

HCID 1200877-Chloro-1H-indole-2-carboxylic acidYield 95.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.40 g (15.2 mmol) of ethyl 7-chloro-2-indolecarboxylate, 100 ml of 2N sodium hydroxide solution and 100 ml of ethanol was refluxed for an hour. The solvent was then distilled off under reduced pressure. Thereafter ice water was added to the residue and the resulting mixture was acidified with conc. hydrochloric acid and extracted three times with ethyl acetate. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 2.85 g (95.8%) of 7-chloro-2-indolecarboxylic acid.

Workup

  1. temperaturewas refluxed for an hour
  2. distillationThe solvent was then distilled off under reduced pressure
  3. additionThereafter ice water was added to the residue
  4. extractionextracted three times with ethyl acetate
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-786a282081cb4a54ba2210921b48ce45
Source dataset
uspto-grants-2001_06
Patent number
US06248772B1

Reaction notes

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