Sodium Hydroxide → 1-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid

HRID 16626Notes

Reaction equation

HRID 16626 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:18]([O:20]CC)=[O:19])=[C:9]1[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CCO.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:18]([OH:20])=[O:19])=[C:9]1[CH3:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 628089Ethyl 1-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylate2×

Product 1

HCID 497872521-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

General Procedure 2 A solution of ethyl 1-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylate (Compound 1, 873 mg, 2.83 mmol) and NaOH (2.2 g, 56 mmol) in EtOH (10 ml) and H2O (10 ml) was heated to 90° C. for 16 h. The reaction was quenched with 6M HCl (10 ml), extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes to 20% MeOH-EtOAc) to yield 1-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid (Compound 2) as a reddish brown solid.

Workup

  1. customThe reaction was quenched with 6M HCl (10 ml)
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes to 20% MeOH-EtOAc)

Sources & evidence

ORD record
ord-1412233c32a84730913c66b3d47092b1
Source dataset
uspto-grants-2010_06
Patent number
US07737173B2

Reaction notes

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