Citric Acid → 1-Methyl-3-phenyl-1H-indole-6-carboxylic acid

HRID 409910Notes

Reaction equation

HRID 409910 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13]C)=[O:12])[CH:9]=2)[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:3]1.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 59626075Methyl 1-methyl-3-phenyl-1H-indole-6-carboxylate

Product 1

HCID 596260201-Methyl-3-phenyl-1H-indole-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of compound 16c (517 mg, 1.95 mmol) and LiOH (187 mg, 7.80 mmol) in THF/MeOH/H2O (4/4/4 mL) was stirred for 4 h. A 15% citric acid solution (20 mL) was added, and the mixture was then extracted with EtOAc (3×). The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue, compound 16d, was dried under reduced pressure for 18 h.

Workup

  1. extractionthe mixture was then extracted with EtOAc (3×)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dry with materialThe residue, compound 16d, was dried under reduced pressure for 18 h.

Sources & evidence

ORD record
ord-ae14e42cba51415d935223c274c6107f
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Reaction notes

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