Sodium Hydroxide → 6-Chloro-2-methyl-1H-indole-3-carboxylic acid

HRID 505080Notes

Reaction equation

HRID 505080 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12](=[O:17])C(F)(F)F)=[C:7]([CH3:11])[NH:8]2)=[CH:4][CH:3]=1.[OH-:18].[Na+]>O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]([OH:17])=[O:18])=[C:7]([CH3:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59657516HCID 59657516, compound

Product 1

HCID 451210656-Chloro-2-methyl-1H-indole-3-carboxylic acidYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.57 g (2.2 mmol) 1-(6-chloro-2-methyl-1H-indol-3-yl)-2,2,2-trifluoro-ethanone in 21.7 ml (86.8 mmol) aqueous 4 M sodium hydroxide solution was heated at reflux for 45 min. After cooling to room temperature the reaction mixture was diluted with water and extracted with tert-butyl methyl ether (2×50 ml). The aqueous layer was cooled to 0-5° C., acidified (pH 1-2) with concentrated aqueous hydrochloric acid solution and extracted with ethyl acetate (3×100 ml). The combined ethyl acetate layers were dried over sodium sulfate and concentrated in vacuo to give the title compound (0.14 g, 31%) as an off-white solid.

Workup

  1. temperatureat reflux for 45 min
  2. extractionextracted with tert-butyl methyl ether (2×50 ml)
  3. temperatureThe aqueous layer was cooled to 0-5° C.
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. dry with materialThe combined ethyl acetate layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16120f2da2c14c6198b8d42f995453a3
Source dataset
uspto-grants-2010_08
Patent number
US07781436B2

Reaction notes

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