Hydrochloric Acid → HCID 69659359, compound

HRID 1829026Notes

Reaction equation

HRID 1829026 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][O:23][C:24]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:25]=1[CH2:26][NH:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[C:33](=O)[O:32][CH2:31]2.Cl>C(COC)OC.CO>[CH3:22][O:23][C:24]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:25]=1[CH2:26][NH:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[C:33](=[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:32][CH2:31]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 321710OxindoleHCID 220615235-{[(2,4-Dimethoxyphenyl)methyl]amino}-2-benzofuran-1(3H)-oneHCID 178418339Butyllithium

Product 1

HCID 69659359HCID 69659359, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of oxindole (555 mg, 4.17 mmol) in anhydrous dimethoxyethane (20 ml) under nitrogen was added 2.5M n-BuLi solution in hexane (3.67 ml, 9.17 mmol), and the resulting mixture was stirred at room temperature for 10 minutes, followed by the addition of 5-(2,4-dimethoxy-benzylamino)-3H-isobenzofuran-1-one (1.0 g, 3.34 mmol). After stirred at room temperature for 2.5 hours the mixture was poured into 1M HCl aqueous solution (100 ml). The resulting solid was separated, washed with water, and dried under vacuum to afford a crude product. Trituration of the crude product with MeOH produced 3-[5-(2,4-dimethoxy-benzylamino)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one as a yellow solid (630 mg, 46%).

Workup

  1. stirringAfter stirred at room temperature for 2.5 hours the mixture
  2. customThe resulting solid was separated
  3. washwashed with water
  4. customdried under vacuum
  5. customto afford a crude product

Sources & evidence

ORD record
ord-2307ffd778194664b8cd67088bcf3946
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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