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

HRID 1976732Notes

Reaction equation

HRID 1976732 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-496beb0490f54e3eaf4c7848af5695b0
Source dataset
uspto-grants-2001_05
Patent number
US06228877B1

Reaction notes

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