Hydrochloric Acid → 6-(4-methylphenyl)-1H-indole-2-carboxylic acid

HRID 1169356Notes

Reaction equation

HRID 1169356 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH:12]=[C:13]([C:17]([O:19]CC)=[O:18])[NH:14]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C.C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH:12]=[C:13]([C:17]([OH:19])=[O:18])[NH:14]3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22990151ethyl 6-(4-methylphenyl)-1H-indole-2-carboxylate

Product 1

HCID 229901346-(4-methylphenyl)-1H-indole-2-carboxylic acidYield 94.3%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Into a mixed solution of ethyl 6-(4-methylphenyl)-1H-indole-2-carboxylate (0.6 g) in ethanol/THF (10/10 ml) was added at room temperature a 2 N aqueous solution of sodium hydroxide (5 ml), and the resulting mixture was stirred for 64 hours. After addition of 1 N hydrochloric acid (15 ml), the reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration of the organic layer under reduced pressure, the precipitated crystals were collected by filtration. The crystals were washed with hexane to obtain 6-(4-methylphenyl)-1H-indole-2-carboxylic acid (509 mg) as colorless crystals.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialwas dried with magnesium sulfate
  6. filtrationAfter concentration of the organic layer under reduced pressure, the precipitated crystals were collected by filtration
  7. washThe crystals were washed with hexane

Sources & evidence

ORD record
ord-4bbccbfadf2d4510a0ebbf47826b46d8
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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