Lithium hydroxide, monohydrate → 2-(7-Cyano-1H-indol-1-yl)acetic acid

HRID 453916Notes

Reaction equation

HRID 453916 reaction equation
O[Li].O.[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[N:13]([CH2:15][C:16]([O:18]CC)=[O:17])[CH:12]=[CH:11]2)#[N:5]>O.C1COCC1>[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[N:13]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:11]2)#[N:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59473725Ethyl 2-(7-cyano-1H-indol-1-yl)acetate

Product 1

HCID 594737242-(7-Cyano-1H-indol-1-yl)acetic acidYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH.H2O (1.4 g, 34.06 mmol, 3.0 equiv.) in water (10 ml) was added at 0° C. to a solution of ethyl 2-(7-cyano-1H-indol-1-yl)acetate (2.6 g, 11.37 mmol, 1.0 equiv.) in THF, and the mixture was stirred for 2 h at RT. When the reaction was complete (TLC monitoring), the mixture was concentrated under vacuum and the residue was taken up in water (50 ml). Extraction with ethyl acetate (50 ml) was carried out, and then the aqueous phase was adjusted to pH≈3-4 with 10% HCl solution. Extraction with DCM (2×50 ml) was then carried out, and the combined organic phases were washed with sat. NaCl solution, dried over Na2SO4 and concentrated under vacuum. The desired product was isolated in the form of a light-yellow solid.

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. extractionExtraction with ethyl acetate (50 ml)
  3. extractionExtraction with DCM (2×50 ml)
  4. washthe combined organic phases were washed with sat. NaCl solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fbd1b87d54834c98b239361f27b9df63
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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