Water → 3-Phenyl-1-(p-toluenesulfonyl)indole-2-carboxylic acid

HRID 128869Notes

Reaction equation

HRID 128869 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[C:8]=2[C:26]([O:28]C(C)(C)C)=[O:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(Cl)(Cl)C(O)=O.O>C(Cl)Cl>[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=3)(=[O:18])=[O:17])[C:8]=2[C:26]([OH:28])=[O:27])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6421Trichloroacetic AcidHCID 18688802t-Butyl 3-phenyl-1-(p-toluenesulfonyl)indole-2-carboxylate

Product 1

HCID 186887843-Phenyl-1-(p-toluenesulfonyl)indole-2-carboxylic acidYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2.55 g of compound J in 10 cc of methylene chloride was added 2.20 g of trichloroacetic acid under ice-cooling and the mixture was stirred for 16 hours. Water was added to the reaction mixture, the desired compound was extracted with ethyl acetate. The extract was dried over magnesium sulfate and distilled to remove the solvent. The crude product thus obtained was purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=3/7) to obtain 2.10 g of 3-phenyl-1-(p-toluenesulfonyl)indole-2-carboxylic acid. Yield: 94.1%.

Workup

  1. temperaturecooling
  2. extractionthe desired compound was extracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. distillationdistilled
  5. customto remove the solvent
  6. customThe crude product thus obtained
  7. customwas purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=3/7)

Sources & evidence

ORD record
ord-b4a3272094b04cfbb7c837b9c034f8db
Source dataset
uspto-grants-1995_11
Patent number
US05464863

Reaction notes

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