Hydrochloric Acid → 3-(5-Amino-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

HRID 1263719Notes

Reaction equation

HRID 1263719 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].C[Si](C)(C)N[Si](C)(C)C.[Na].[NH2:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[C:27](=O)[O:26][CH2:25]2.Cl.C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[C:27](=[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:26][CH2:25]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 321710OxindoleHCID 516892Sodium BicarbonateHCID 7206695-AminophthalideHCID 45051731Sodium hexamethyidisilazane

Product 1

HCID 696596273-(5-Amino-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-oneYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution containing oxindole (0.5 g, 3.76 mmol) in 7.5 mL DMF was added 7.51 mL of sodium hexamethyldisilazane (1.0 M in THF) over 3 min. After stirring 10 min at room temperature, a solution of 5-aminophthalide (0.672 g, 4.51 mmol) in 4.0 mL DMF was added over 3 min. The reaction was stirred for 30 min at room temperature and then poured into 4% aqueous HCl solution to give a yellow cloudy solution. After stirring the mixture 3 min, the solution was made basic by adding saturated NaHCO3. The yellow solid was filtered, washed with H2O, and then dissolved in CHCl3/MeOH. The solvent was removed in vacuo and the solid purified by chromatography (silica gel, CHCl3/MeOH, 95:5) to give the title compound (345 mg, 35%) as a yellow solid.

Workup

  1. stirringThe reaction was stirred for 30 min at room temperature
  2. customto give a yellow cloudy solution
  3. stirringAfter stirring the mixture 3 min
  4. filtrationThe yellow solid was filtered
  5. washwashed with H2O
  6. dissolutiondissolved in CHCl3/MeOH
  7. customThe solvent was removed in vacuo
  8. customthe solid purified by chromatography (silica gel, CHCl3/MeOH, 95:5)

Sources & evidence

ORD record
ord-6afc935273a143f4a40ac693d15d664b
Source dataset
uspto-grants-2003_04
Patent number
US06541504B1

Reaction notes

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