Ethylene Glycol → HCID 58306977, compound

HRID 1909895Notes

Reaction equation

HRID 1909895 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1C=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:12]=1C#N)[CH:6]=[CH:5]2.[OH-:23].[Na+].Cl.[CH2:26]([OH:29])[CH2:27]O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:12]=[CH:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][C:27]=1[C:26]([OH:29])=[O:23])[CH:6]=[CH:5]2

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58306769HCID 58306769, compound

Product 1

HCID 58306977HCID 58306977, compound

Conditions

Temperature
180 °C

Procedure

To a mixture of 2-(5-chloro-1H-indol-1-yl)-5-(trifluoromethyl)benzonitrile (1.66 g) and ethylene glycol (18 mL) was added a 1 M aqueous sodium hydroxide solution (26 mL) at room temperature, followed by stirring at 180° C. for 16 hours. The reaction mixture was cooled to room temperature and neutralized by adding 1 M hydrochloric acid (26 mL), followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 2-(5-chloro-1H-indol-1-yl)-5-(trifluoromethyl)benzoic acid (1.67 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-15eec00600e9414abbce9d8990a48c7b
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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