Hydrochloric Acid → HCID 67292072, compound

HRID 511841Notes

Reaction equation

HRID 511841 reaction equation
FC(F)(F)[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:11][CH:12]=2)[N:7]([CH3:18])[CH:6]=1)=[O:4].[OH-:21].[Na+].Cl>>[CH3:18][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:5]([C:3]([OH:4])=[O:21])=[CH:6]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86664378HCID 86664378, compound

Product 1

HCID 67292072HCID 67292072, compoundYield 67%

Procedure

A mixture of 2,2,2-trifluoro-1-(1-methyl-6-(trifluoromethyl)-1H-indol-3-yl)ethanone (195 mg, 0.66 mmol) and 20% aqueous sodium hydroxide solution (5 mL) was refluxed with stirring for 10 hours. After cooling to room temperature, the mixture was poured into 1 M hydrochloric acid, and the aqueous phase was extracted with ethyl acetate (twice). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residual solid was washed with 2-propanol to give 107 mg (67% yield) of the title compound as a pale orange solid:

Workup

  1. temperaturewas refluxed
  2. extractionthe aqueous phase was extracted with ethyl acetate (twice)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. washThe residual solid was washed with 2-propanol

Sources & evidence

ORD record
ord-bb184aee92cb45b1ae2d9de61c491f96
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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