Potassium Hydroxide → 3-(4-Chlorophenyl)-4-(methylsulfanyl)-1h-indole-2-carboxylic acid

HRID 857319Notes

Reaction equation

HRID 857319 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[S:17][CH3:18])[NH:10][C:9]=2[C:19]([O:21]CC)=[O:20])=[CH:4][CH:3]=1.[OH-].[K+]>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[S:17][CH3:18])[NH:10][C:9]=2[C:19]([OH:21])=[O:20])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21867418Ethyl 3-(4-chlorophenyl)-4-(methylsulfanyl)-1h-indole-2-carboxylate

Product 1

HCID 218674693-(4-Chlorophenyl)-4-(methylsulfanyl)-1h-indole-2-carboxylic acidYield 101.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the ester of Step 4 (1.5 g) in EtOH (15 mL) was added 1N KOH solution (13 mL). The reaction mixture was stirred at reflux for 1 hour. The organic solvent was removed by evaporation and the aqueous solution was acidified with 3N HCl and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated to give the title compound as a white solid (1.4 g).

Workup

  1. temperatureat reflux for 1 hour
  2. customThe organic solvent was removed by evaporation
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2488214679e247d4b97f79b0d5521fa6
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

Loading…