6-Chloro-1,3-dihydroindol-2-one → HCID 12032310, compound

HRID 853851Notes

Reaction equation

HRID 853851 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Br-:12].[Br-:13].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CC(O)(C)C.O>[Br:12][C:6]1([Br:13])[C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[NH:8][C:7]1=[O:11]

Participants

5

Reactant 2

HCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 21124087Pyridiniumtribromide

Product 1

HCID 12032310HCID 12032310, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

At room temperature, to a solution of 6-chlorooxindole (10.0 g, 59.7 mmol ) in t-BuOH (500 mL) and water (2.6 mL) was added pyridinium tribromide (57.25 g, 79 mmol, 3 eq) and the reaction was stirred for 3.5 hr. The reaction was diluted with water (500 mL) and extracted with EtOAc (3×). The combined organic extracts were washed with sat. aq. NaHCO3 (3×), dried over MgSO4, filtered and concentrated to give the title compound as a tan solid (19.66 g, 100% yield). NMR (400 MHz, DMSO-d6): consistent. MS: (API-ES+) m/z 325 [M+H].

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic extracts were washed with sat. aq. NaHCO3 (3×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-82664a5753f84d0eb61be1dd3d0b6694
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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