Hydrochloric Acid → 5-(Pyrrolidine-1-sulfonyl)-1,3-dihydro-indol-2-one

HRID 49109Notes

Reaction equation

HRID 49109 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)(=[O:4])=[O:3].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.N1C=CC=CC=1.Cl>ClCCl.C(OCC)(=O)C>[N:15]1([S:2]([C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8]3)(=[O:4])=[O:3])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31268PyrrolidineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 220421535-(Pyrrolidine-1-sulfonyl)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 5-chlorosulfonyl-2-oxindole (1.62 g, 7 mmol), pyrrolidine (0.701 mL, 8.4 mmol) and pyridine (1 mL) in dichloromethane (20 mL) was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate (300 mL) and made acidic with 1N hydrochloric acid (16 mL). The organic layer was then washed with sodium bicarbonate and brine, dried and concentrated. The residue was washed with ethanol (3 mL). It was then purified by chromatography on silica gel eluting with methanol:dichloromethane 1:9 to give 0.432 g (27%)-5-(pyrrolidine-1-sulfonyl)-1,3-dihydro-indol-2-one.

Workup

  1. washThe organic layer was then washed with sodium bicarbonate and brine
  2. customdried
  3. concentrationconcentrated
  4. washThe residue was washed with ethanol (3 mL)
  5. customIt was then purified by chromatography on silica gel eluting with methanol:dichloromethane 1:9

Sources & evidence

ORD record
ord-58d6d32a81db491db7056d18bd9d5ada
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

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