HCID 19419318, compound → HCID 22079512, compound

HRID 864873Notes

Reaction equation

HRID 864873 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]=[CH2:10])[C:4]=1[NH:11][C:12](=[O:28])[CH2:13][CH:14]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:21][C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2.[H][H]>O1CCCC1.[Pd]>[CH2:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[NH:11][C:12](=[O:28])[CH2:13][CH:14]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=2[O:21][C:22]2[C:27]1=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:10]

Participants

5

Reactant 2

HCID 19419318HCID 19419318, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22079512HCID 22079512, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 258 mg (0.62 mmol) of N-(2-methoxy-6-vinylphenyl)-2-(9H-xanthen-9-yl)acetamide in 54 ml of tetrahydrofuran was vigorously stirred at room temperature for 10 hours in the presence of 20 mg of 10% palladium on charcoal in a stream of hydrogen. The reaction mixture was filtered with the aid of Celite and the catalyst was washed with tetrahydrofuran. The filtrate and the washings were combined and concentrated. The residue was recrystallized from a mixture of dichloromethane and hexane to give 99 mg (57%) of the title compound as crystals.

Workup

  1. filtrationThe reaction mixture was filtered with the aid of Celite
  2. washthe catalyst was washed with tetrahydrofuran
  3. concentrationconcentrated
  4. customThe residue was recrystallized from a mixture of dichloromethane and hexane

Sources & evidence

ORD record
ord-84c099072d004c879a891de31924135d
Source dataset
uspto-grants-1996_10
Patent number
US05563169

Reaction notes

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