Sodium Hydroxide → 6-(Methylthio)-1H-indole-2-carboxylic acid

HRID 442751Notes

Reaction equation

HRID 442751 reaction equation
C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([S:14][CH3:15])[CH:8]=2)=[O:4].[OH-].[Na+]>>[CH3:15][S:14][C:9]1[CH:8]=[C:7]2[C:12]([CH:13]=[C:5]([C:3]([OH:4])=[O:2])[NH:6]2)=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 4715405202584-20-1

Product 1

HCID 39071736-(Methylthio)-1H-indole-2-carboxylic acidYield 91%

Procedure

A mixture of methyl-6-methylsulfanyl-1H-indole-2-carboxylate (11.2 g, 51 mmol) and 2N NaOH (125 ml) was heated to reflux temperature for 30 minutes. The clear solution was cooled, and extracted with EtOAc. The aqueous fraction was acidified with concentrated HCl to pH=1, and the precipitate which formed, was filtered and dried to give 6-Methylsulfanyl-1H-indole-2-carboxylic acid (9.6 g, 91.0%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperature for 30 minutes
  3. temperatureThe clear solution was cooled
  4. extractionextracted with EtOAc
  5. customthe precipitate which formed
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-145ccd111c3944c6a51053116d174ca3
Source dataset
uspto-grants-1999_04
Patent number
US05891901

Reaction notes

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