Hydrochloric Acid → 5-Chloro-3-(5-dimethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydroindol-2-one

HRID 1829032Notes

Reaction equation

HRID 1829032 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[Li]CCCC.CCCCCC.[CH3:23][N:24]([CH3:35])[C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[C:30](=O)[O:29][CH2:28]2.Cl.[OH-].[Na+]>C(COC)OC.CCOC(C)=O.CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:30]1[C:31]2[C:27](=[CH:26][C:25]([N:24]([CH3:35])[CH3:23])=[CH:33][CH:32]=2)[CH2:28][O:29]1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 14798Sodium HydroxideHCID 1528015-ChlorooxindoleHCID 34010695-DimethylaminophthalideHCID 178418339Butyllithium

Product 1

HCID 688358045-Chloro-3-(5-dimethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydroindol-2-oneYield 49%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5-chlorooxindole (1.18 g, 7.05 mmol) in anhydrous dimethoxyethane (20 ml) under nitrogen was added 2.5M n-BuLi solution in hexane (6.2 ml, 15.5 mmol). The mixture was stirred at room temperature for 10 minutes, and then 5-dimethylamino-3H-isobenzofuran-1-one (1.00 g, 5.64 mmol) was added. After stirred at room temperature for 3 hours, the mixture was poured into 0.5M HCl aqueous solution (80 ml) with stirring and then basified with NaOH aqueous solution. The solid was filtered, washed with water, and dried under vacuum to give a crude product. Trituration of the crude product with MeOH and EtOAc provided 5-chloro-3-(5-dimethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one as a yellow solid (0.90 g, 49%).

Workup

  1. stirringAfter stirred at room temperature for 3 hours
  2. stirringwith stirring
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried under vacuum
  6. customto give a crude product

Sources & evidence

ORD record
ord-f91380fe9d7f498d861a315152708c16
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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