Sodium Hydroxide → N-(3-Hydroxy-4-methoxybenzenesulphonyl)-1,2-dihydroindole

HRID 2141Notes

Reaction equation

HRID 2141 reaction equation
CS([O:5][C:6]1[CH:7]=[C:8]([S:14]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18]2)(=[O:16])=[O:15])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13])(=O)=O.[OH-].[Na+]>>[OH:5][C:6]1[CH:7]=[C:8]([S:14]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18]2)(=[O:16])=[O:15])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 19689647N-(3-methanesulphonyloxy-4-methoxybenzenesulphonyl)-1,2-dihydroindole

Product 1

HCID 19689638N-(3-Hydroxy-4-methoxybenzenesulphonyl)-1,2-dihydroindoleYield 100.5%

Procedure

A solution of N-(3-methanesulphonyloxy-4-methoxybenzenesulphonyl)-1,2-dihydroindole (1 g) and saturated aqueous sodium hydroxide solution (2 ml) was heated at 85°-90° C. for 2 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (5 ml) and water (10 ml). The aqueous phase was acidified with 2N HCl and extracted with ethyl acetate (2×10 ml). The combined organic phases were dried over magnesium sulphate and concentrated in vacuo to yield a clear oil. Purification by column chromatography eluting with dichloromethane afforded the desired product as a white solid (0.8 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (5 ml) and water (10 ml)
  3. extractionextracted with ethyl acetate (2×10 ml)
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customto yield a clear oil
  7. customPurification by column chromatography
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-ff57e297cfdc46e5b5870e456c42198a
Source dataset
uspto-grants-1998_03
Patent number
US05728712

Reaction notes

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