Methanol → HCID 22490570, compound

HRID 2180871Notes

Reaction equation

HRID 2180871 reaction equation
[OH-].[Na+].CO.C[O:6][C:7](=[O:23])[CH2:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:15][CH:16]=2)[NH:11][C:10]=1[CH3:22]>O>[CH3:22][C:10]1[NH:11][C:12]2[C:17]([C:9]=1[CH2:8][C:7]([OH:23])=[O:6])=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:19])[F:21])[CH:13]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 697331362-(2-methyl-6-trifluoromethyl-1H-indol-3-yl)acetic acid methyl ester

Product 1

HCID 22490570HCID 22490570, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2 N sodium hydroxide aqueous solution (1 ml) and methanol (1 ml) were added to the obtained 2-(2-methyl-6-trifluoromethyl-1H-indol-3-yl)acetic acid methyl ester, and the mixture was heated to reflux for one hour. Water was added to the reaction mixture, which was then rendered acidic with concentrated aqueous hydrochloric acid, extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure, to obtain 79 mg of the title compound as a colorless powder (6% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for one hour
  3. extractionrendered acidic with concentrated aqueous hydrochloric acid, extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-468ceb4f212c415989bb0e81e43c60a8
Source dataset
uspto-grants-2005_05
Patent number
US06887890B2

Reaction notes

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