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

HRID 38433Notes

Reaction equation

HRID 38433 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-9880896beb274f0dadee3df413c72af1
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

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