Hydrochloric Acid → 3-(5-Dimethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Li]CCCC.CCCCCC.[CH3:22][N:23]([CH3:34])[C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:29](=O)[O:28][CH2:27]2.Cl.[OH-].[Na+]>COCCOC>[CH3:22][N:23]([CH3:34])[C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:29](=[C:3]1[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]1=[O:10])[O:28][CH2:27]2Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of oxindole (938 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 1M 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), collected by filtration and dried to give title compound (990 mg, 60%) as a bright yellow powder.
Workup
- temperatureto warm to room temperature under nitrogen
- stirringstirring
- waitwas continued for 3 hours
- customThe yellow precipitate which formed
- filtrationwas collected by filtration
- washwashed with water
- customdried under vacuum
- customThe solid obtained
- customwas triturated with hot MeOH (20 mL)
- filtrationcollected by filtration
- customdried
Sources & evidence
- ORD record
- ord-82783a6807fa475285566b3f78c6e02d
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07531665B2
Reaction notes
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