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

HRID 2266177Notes

Reaction equation

HRID 2266177 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-0d5d3f591d71466092c9f59dcd3536b3
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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