Potassium Hydroxide → HCID 68432545, compound

HRID 2235125Notes

Reaction equation

HRID 2235125 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][N:11]2[S:14]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[O:24][CH3:25])(=[O:16])=[O:15])=[CH:7][CH:6]=1)=[O:4].[OH-].[K+]>CO.O1CCCC1>[Cl:23][C:21]1[CH:20]=[CH:19][C:18]([O:24][CH3:25])=[C:17]([S:14]([N:11]2[C:12]3[C:8](=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:13]=3)[CH2:9][CH2:10]2)(=[O:15])=[O:16])[CH:22]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 68434888HCID 68434888, compound

Product 1

HCID 68432545HCID 68432545, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (2.2 g, 5.8 mmol) in methanol (6 ml) and tetrahydrofuran (6 ml) was treated with 3N KOH (6 ml, 3 equiv.) and stirred at room temperature for 24 hours. The organic solvents were evaporated and the aqueous slurry treated with HCl 3N so as to reach pH 3. The white precipitate was filtered washing with methanol and water and dried under high vacuum to yield 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid as an off-white solid, 1.9 g (88%). This was used as such in the following reaction.

Workup

  1. customThe organic solvents were evaporated
  2. additionthe aqueous slurry treated with HCl 3N so as
  3. filtrationThe white precipitate was filtered
  4. washwashing with methanol and water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-806ce03b805048b18dfa4dc437a1dd71
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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