Hydrochloric Acid → 6-Chloro-1-(propan-2-yl)-1H-indole-3-carboxylic acid

HRID 1816162Notes

Reaction equation

HRID 1816162 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:14](=[O:19])C(F)(F)F)=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[OH-:20].[Na+].Cl>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:14]([OH:19])=[O:20])=[CH:7][N:8]2[CH:11]([CH3:12])[CH3:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 224972541-[6-Chloro-1-(1-methylethyl)-1H-indol-3-yl]-2,2,2-trifluoroethanone

Product 1

HCID 224972296-Chloro-1-(propan-2-yl)-1H-indole-3-carboxylic acidYield 99%

Conditions

Temperature
110 °C

Procedure

A mixture of 1-(6-chloro-1-isopropyl-1H-indol-3-yl)-2,2,2-trifluoro-ethanone (475 mg, 1.64 mmol) in a 20% aqueous sodium hydroxide solution was heated at 110° C. for 18 h. At this time, the reaction was cooled to 25° C. and treated with a 1N aqueous hydrochloric acid solution. This solution was extracted with ethyl acetate (1×50 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 6-chloro-1-isopropyl-1H-indole-3-carboxylic acid (385 mg, 99%) as a yellow solid: mp 206-208° C.; EI-HRMS m/e calcd for C12H12ClNO2 (M+) 237.0056, found 237.0554.

Workup

  1. temperatureAt this time, the reaction was cooled to 25° C.
  2. extractionThis solution was extracted with ethyl acetate (1×50 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74d596ab547c4744b2752aa8ef426505
Source dataset
uspto-grants-2005_04
Patent number
US06881844B2

Reaction notes

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