Sodium Hydroxide → HCID 22497228, compound

HRID 1816127Notes

Reaction equation

HRID 1816127 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:14])[CH:12]=2)[C:7]([C:15](=[O:20])C(F)(F)F)=[CH:6]1)[CH2:2][CH2:3][CH3:4].[OH-:21].[Na+]>O>[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:14])[CH:12]=2)[C:7]([C:15]([OH:20])=[O:21])=[CH:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22497248HCID 22497248, compound

Product 1

HCID 22497228HCID 22497228, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1-(1-butyl-6-chloro-1H-indol-3-yl)-2,2,2-trifluoro-ethanone (283.7 mg, 0.81 mmol) in a 20% aqueous sodium hydroxide solution (2.7 mL) was heated under reflux for 17 h. At this time, the reaction was cooled to 25° C. and was diluted with water (75 mL). This mixture was extracted with diethyl ether (1×50 mL). The aqueous layer was acidified to pH=1 with concentrated hydrochloric acid and then extracted with ethyl acetate (1×75 mL). The combined organic layers were washed with water (1×50 mL) and a saturated aqueous sodium chloride solution (1×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford 1-butyl-6-chloro-1H-indole-3-carboxylic acid (141.4 mg, 69.6%) as a pale orange solid: mp 149-151° C.; EI-HRMS m/e calcd for C13H14ClNO2 (M+) 251.0713, found 251.0721.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 17 h
  3. extractionThis mixture was extracted with diethyl ether (1×50 mL)
  4. extractionextracted with ethyl acetate (1×75 mL)
  5. washThe combined organic layers were washed with water (1×50 mL)
  6. dry with materiala saturated aqueous sodium chloride solution (1×50 mL), dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8398853db2434b83b569603b1fa967a6
Source dataset
uspto-grants-2005_04
Patent number
US06881844B2

Reaction notes

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