Hydrochloric Acid → 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid

HRID 81848Notes

Reaction equation

HRID 81848 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH3:15])=[CH:12][C:11]([O:16][CH3:17])=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=2)=[O:5])C.[OH-].[K+].Cl>C(O)C.O>[CH3:17][O:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[C:18]([F:20])([F:21])[F:19])[NH:7][C:6]([C:4]([OH:5])=[O:3])=[C:14]2[CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 595986695-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 595986355-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acidYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester (3.0 g, 10 mmol) was dissolved in 10 ml absolute ethanol, and a solution of KOH (1.7 g, 30 mmol) in 7 ml water was added. The reaction mixture was heated to reflux for 2.5 hours, then cooled, acidified slowly with 6 N HCl to pH=2, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give 2.0 g, (73%) 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2.5 hours
  3. temperaturecooled
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cf4a7350780e493d9d0249d46c930af2
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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