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

HRID 1829013
Notes
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Reaction equation

HRID 1829013 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.[C:28]1([C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][O:30]1)=O.Cl>C1COCC1.O>[C:28]1(=[C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=3)[NH:8][C:7]2=[O:12])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][O:30]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6885PhthalideHCID 15142865-MethoxyoxindoleHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 696593173-(2-Benzofuran-1(3H)-ylidene)-5-methoxy-1,3-dihydro-2H-indol-2-oneYield 46%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 5-methoxyoxindole (100 mg, 0.61 mmol) in anhydrous THF (5 ml) under nitrogen was added 1.0M LiHMDS/THF solution (1.3 ml, 1.3 mmol). The mixture was stirred at room temperature for 10 minutes, and phthalide (74 mg, 0.55 mmol) was added. The mixture was stirred at room temperature for 5 hours and was then poured into a mixture of THF (10 ml) and 2M HCl (10 ml). The mixture was heated at 45° C. for 30 minutes, cooled to room temperature, and poured into water (125 ml). The resulting solid was separated, washed with water and dried under vacuum to give 3-(3H-Isobenzofuran-1-ylidene)-5-methoxy-1,3-dihydro-indol-2-one (70 mg, 46%).

Workup

  1. stirringThe mixture was stirred at room temperature for 5 hours
  2. temperatureThe mixture was heated at 45° C. for 30 minutes
  3. temperaturecooled to room temperature
  4. customThe resulting solid was separated
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-e9ef2712fb87429c83c586f0d17a862f
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07060844B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes