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

HRID 352306Notes

Reaction equation

HRID 352306 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:32](=[CH:33][CH:34]=1)[C:30](=O)[O:29][CH2:28]2.Cl.[OH-].[Na+]>COCCOC>[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:32]2[C:27](=[CH:26][C:25]([N:24]([CH3:35])[CH3:23])=[CH:34][CH:33]=2)[CH2:28][O:29]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1528015-ChlorooxindoleHCID 34010695-DimethylaminophthalideHCID 178418244HCID 178418244, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-chlorooxindole (1.18 mg, 7.05 mmol) in 20 mL of DME was cooled to 0° C., and treated with 6.2 mL of 2.5M n-BuLi/hexane solution (15.5 mmol) dropwise under nitrogen. The mixture was stirred at 0° C. for 10 minutes. 5-dimethylaminophthalide (1.0 g, 5.64 mmol) was added as one portion. The mixture was allowed to warm to room temperature under nitrogen and stirring was continued for 3 hours. The cloudy mixture was then slowly added into 0.5M aqueous HCl solution (0° C.) with vigorous stirring. The resulting mixture was neutralized with 1 M NaOH solution until pH=9. The yellow precipitate which formed was collected by filtration, washed with water, dried under vacuum. The solid obtained was triturated with hot MeOH (20 mL) followed by ethyl acetate (10 mL), collected by filtration and dried to give title compound (900 mg, 49%) as a bright yellow powder.

Workup

  1. temperatureto warm to room temperature under nitrogen
  2. stirringstirring
  3. waitwas continued for 3 hours
  4. customThe yellow precipitate which formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried under vacuum
  8. customThe solid obtained
  9. customwas triturated with hot MeOH (20 mL)
  10. filtrationcollected by filtration
  11. customdried

Sources & evidence

ORD record
ord-677aabd26af94b698150c499366bd809
Source dataset
uspto-grants-2004_06
Patent number
US06747025B1

Reaction notes

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