HCID 18442913, compound → HCID 18442914, compound

HRID 458726Notes

Reaction equation

HRID 458726 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][CH2:13][O:14][C:15]3[CH:30]=[CH:29][C:18]([CH:19]=[C:20]([C:25]([O:27][CH3:28])=[O:26])[C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:16]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H][H]>CO.O1CCOCC1.[Pd]>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][CH2:13][O:14][C:15]3[CH:30]=[CH:29][C:18]([CH2:19][CH:20]([C:25]([O:27][CH3:28])=[O:26])[C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:16]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 18442913HCID 18442913, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18442914HCID 18442914, compoundYield 91.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of dimethyl 4-[2-(6-quinolinoxy)ethoxy]benzylidenemalonate (2.23 g, 5.47 mmol) in a mixture of methanol (20 ml) and 1,4-dioxane (150 ml) is added 5% palladium on charcoal (1.20 g). Then the mixture is stirred under an atmosphere of hydrogen at room temperature until hydrogen uptake ceased. The solution is filtered through Celite, and the filtrate is evaporated under a vacuum. The residue is crystallized from ethyl acetate to give the title compound (2.04 g, 90%). HRMS calcd for C23H27NO6: 413.4670. Found: 413.4672. MA calcd for C23H27NO6: C, 66.81%; H, 6.58%; N, 3.39%. Found: C, 66.53%; H, 6.55%; N, 3.36%.

Workup

  1. filtrationThe solution is filtered through Celite
  2. customthe filtrate is evaporated under a vacuum
  3. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-941d4cf546634a46a2113048ceb37863
Source dataset
uspto-grants-2007_03
Patent number
US07192970B2

Reaction notes

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