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

HRID 564976Notes

Reaction equation

HRID 564976 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-3e6cf5179acc4554936f30801a1b4064
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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