Methanol → 2-Methyl-1-(1-phenylethyl)-1H-indole-3-carboxylic acid

HRID 1526951Notes

Reaction equation

HRID 1526951 reaction equation
CO.[CH3:3][C:4]1[N:5]([CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])[C:6]2[C:11]([C:12]=1[C:13]([O:15]CC)=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.[OH-].[K+]>O>[CH3:3][C:4]1[N:5]([CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])[C:6]2[C:11]([C:12]=1[C:13]([OH:15])=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 89740220ethyl 2-methyl-1-(1-phenylethyl)-1H-indole-3-carboxylate

Product 1

HCID 897404232-Methyl-1-(1-phenylethyl)-1H-indole-3-carboxylic acidYield 54.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixed solution of methanol and water (4 mL), ethyl 2-methyl-1-(1-phenylethyl)-1H-indole-3-carboxylate (300 mg, 0.98 mmol) and potassium hydroxide (546 mg, 9.76 mmol) was added. The mixture was refluxed with stirring for 4 hours. The reaction mixture was concentrated to give a residue. To the residue, water (10 mL) was added and the mixture was extracted with dichloromethane (20 mL×3). The organic phase was concentrated to give crude product 2-methyl-1-(1-phenylethyl)-1H-indole-3-carboxylic acid (150 mg). LRMS (M−H)− m/z: calcd 279.13. found 279.

Workup

  1. temperatureThe mixture was refluxed
  2. concentrationThe reaction mixture was concentrated
  3. customto give a residue
  4. extractionthe mixture was extracted with dichloromethane (20 mL×3)
  5. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-a9d918f1177f42d5b65d2cad50cc21c7
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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