Sodium Hydroxide → 2-[5-Cyano-4-(trifluoromethyl)-1H-indol-1-yl]propanoic acid

HRID 2102074Notes

Reaction equation

HRID 2102074 reaction equation
[C:1]([C:3]1[C:4]([C:18]([F:21])([F:20])[F:19])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]([CH3:17])[C:13]([O:15]C)=[O:14])[CH:7]=[CH:6]2)#[N:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([C:3]1[C:4]([C:18]([F:21])([F:20])[F:19])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]([CH3:17])[C:13]([OH:15])=[O:14])[CH:7]=[CH:6]2)#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57800469Methyl 2-(5-cyano-4-(trifluoromethyl)-1H-indol-1-yl)propanoate

Product 1

HCID 578000922-[5-Cyano-4-(trifluoromethyl)-1H-indol-1-yl]propanoic acidYield 99.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To methyl 2-[5-cyano-4-(trifluoromethyl)-1H-indol-1-yl]propanoate (0.055 g, 0.185 mmol) in 1:1 THF/MeOH (4 mL) was added 5N NaOH (0.185 mL) and the resulting mixture was heated to 60° C. for 30 min. The cooled mixture was partitioned between Et2O and 0.1 N HCl. The separated organic portion was washed with brine, dried over Na2SO4, and filtered. Concentration afforded the title compound (0.052 g, 99% yield): MS (APCl) m/z 283 (M+1).

Workup

  1. customThe cooled mixture was partitioned between Et2O and 0.1 N HCl
  2. washThe separated organic portion was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationConcentration

Sources & evidence

ORD record
ord-df9891d15fb14f1ca4af9e7a3b23e20f
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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