Sodium Hydroxide → 6-chloro-1H-indole-3-carboxylic acid

HRID 1097827Notes

Reaction equation

HRID 1097827 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11](=[O:16])C(F)(F)F)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[OH-:17].[Na+]>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:16])=[O:17])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 224972521-(6-Chloro-3-indolyl)-2,2,2-trifluoroethanone

Product 1

HCID 184532356-chloro-1H-indole-3-carboxylic acidYield 78%

Procedure

A mixture of 1.3 g (5.3 mmol) 1-(6-chloro-1H-indol-3-yl)-2,2,2-trifluoro-ethanone and 26.5 ml of a 4 M aqueous solution of sodium hydroxide was heated at reflux for 4.5 h. The mixture was cooled to room temperature and washed with two 100-ml portions of tert-butyl methyl ether. The aqueous layer was acidified to pH 2-3 by addition of concentrated hydrochloric acid solution at 0° C. Extraction with three 100-ml portions of tert-butyl methyl ether, drying over sodium sulfate, filtration and concentration in vacuo gave 0.80 g (78%) of the crude title compound as a brown solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4.5 h
  3. washwashed with two 100-ml portions of tert-butyl methyl ether
  4. additionThe aqueous layer was acidified to pH 2-3 by addition of concentrated hydrochloric acid solution at 0° C
  5. extractionExtraction with three 100-ml portions of tert-butyl methyl ether
  6. dry with materialdrying over sodium sulfate, filtration and concentration in vacuo

Sources & evidence

ORD record
ord-34461d2903f04f74a4b01e57c93ff656
Source dataset
uspto-grants-2012_03
Patent number
US08143281B2

Reaction notes

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