Hydrochloric Acid → 3-(2-Benzofuran-1(3H)-ylidene)-4-methyl-1,3-dihydro-2H-indol-2-one

HRID 1828992Notes

Reaction equation

HRID 1828992 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:11])[NH:6]2.[C:12]1([C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][O:14]1)=O.C[Si](C)(C)N[Si](C)(C)C.[Na].Cl>CN(C=O)C>[C:12]1(=[C:4]2[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[CH3:1])[NH:6][C:5]2=[O:11])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][O:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6885PhthalideHCID 125793824-Methyl-1,3-dihydro-2H-indol-2-oneHCID 45051731Sodium hexamethyidisilazane

Product 1

HCID 696593483-(2-Benzofuran-1(3H)-ylidene)-4-methyl-1,3-dihydro-2H-indol-2-oneYield 1.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution containing 4-methyloxindole (0.15 g, 1.02 mmol) and phthalide (0.178 g, 1.33 mmol) in 3.0 mL DMF was added 2.14 mL of sodium hexamethyldisilazane (1.0 M in tetrahydrofuran (THF)) over 1 min. The solution was stirred at room temperature for 30 min and then poured into 50 mL of 4% HCl to give a yellow solid. The aqueous mixture was extracted with EtOAc and the organic phase washed with saturated NaHCO3, H2O, dilute HCl, brine and the solution dried with Na2SO4. The solvent was removed in vacuo and the solid obtained was purified by chromatography (silica gel, CHCl3/EtOAc, 7:3). The solid obtained was recrystallized from EtOAc/hexanes to afford the title compounds (3.8 mg) as a yellow solid.

Workup

  1. customto give a yellow solid
  2. extractionThe aqueous mixture was extracted with EtOAc
  3. washthe organic phase washed with saturated NaHCO3, H2O, dilute HCl, brine
  4. dry with materialthe solution dried with Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe solid obtained
  7. customwas purified by chromatography (silica gel, CHCl3/EtOAc, 7:3)
  8. customThe solid obtained
  9. customwas recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-e341d320d68c4800b178122c6bf5d1ba
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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