Lithium Hydroxide → Indole-2-carboxylic acid

HRID 83636Notes

Reaction equation

HRID 83636 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12]CC)=[O:11].[OH-].[Li+]>C1COCC1.O.C(OCC)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=[O:11]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 72899Indole-2-carboxylic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1H-indole-2-carboxylate (3.0 g, 15.86 mmol) and lithium hydroxide, H2O (3.33 g, 79 mmol) were dissolved in THF (Ratio: 1.000, Volume: 10 ml) and Water (Ratio: 2, Volume: 20.00 ml). The reaction was stirred overnight. The reaction was diluted with water and diethyl ether. The water layer was washed with diethyl ether twice. The aqueous layer was acidified to pH 2 using 2N HCl. The suspension was extracted using ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to obtain product. (Yield: 2.39 g, white solid) 1H-NMR (400 MHz, DMSO-d6) 12.90, 11.70, 7.60, 7.40, 7.24-7.14, 7.07-6.98

Workup

  1. washThe water layer was washed with diethyl ether twice
  2. extractionThe suspension was extracted
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain product

Sources & evidence

ORD record
ord-a0689db6e8bf41ab95e1826cfcad56d5
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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