Hydrochloric Acid → 6-chloro-1H-indole-3-carboxylic acid

HRID 1711334Notes

Reaction equation

HRID 1711334 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].[K+].Cl>>[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

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 224972521-(6-Chloro-3-indolyl)-2,2,2-trifluoroethanone

Product 1

HCID 184532356-chloro-1H-indole-3-carboxylic acidYield 96%

Procedure

A solution of 21.6 g (87.2 mmol) 1-(6-chloro-1H-indol-3-yl)-2,2,2-trifluoro-ethanone in 110 ml of a 4 M aqueous solution of potassium hydroxide was heated at reflux for 2 h. After cooling to 0° C. neutralisation with 36.7 ml of a concentrated aqueous hydrochloric acid solution a white solid precipitated from the solution. The solid was collected by filtration and washed with water. Drying in high vacuo at 80° C. gave 16.4 g (96%) of the title compound as a light yellow solid.

Workup

  1. temperatureat reflux for 2 h
  2. customprecipitated from the solution
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customDrying in high vacuo at 80° C.

Sources & evidence

ORD record
ord-db96d9d0424643cbb540cdc7fc8a73bd
Source dataset
uspto-grants-2010_09
Patent number
US07790752B2

Reaction notes

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