Lithium hydroxide, monohydrate → 4-Hydroxy-1-methyl-1H-indole-2-carboxylic acid

HRID 749303Notes

Reaction equation

HRID 749303 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14]CC)=[O:13])[N:6]2[CH3:11].O[Li].O.OS([O-])(=O)=O.[K+]>C1COCC1.O>[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[N:6]2[CH3:11]

Participants

6

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 516920Potassium bisulfateHCID 10130663Ethyl 4-hydroxy-1-methyl-1H-indole-2-carboxylate

Product 1

HCID 102197584-Hydroxy-1-methyl-1H-indole-2-carboxylic acidYield 68.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-hydroxy-1-methyl-1H-indole-2-carboxylate (0.20 g) in THF (20 mL) was added LiOH.H2O (0.1 g) in water (20 mL) and the resulting two phase solution was stirred at room temperature under nitrogen for 4 hr. The reaction mixture was acidified with KHSO4 and the product was extracted into EtOAc, washed with brine, dried over MgSO4, and concentrated. The residue was chromatographed over silica gel with a mixture of EtOAc and hexane to give 0.12 g of the title compound. MS ES (M++H)=192.

Workup

  1. extractionthe product was extracted into EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica gel with a mixture of EtOAc and hexane

Sources & evidence

ORD record
ord-e810149489c74e7fa991868e3fe86a55
Source dataset
uspto-grants-2008_07
Patent number
US07402604B2

Reaction notes

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