Methyl 6-[1-(3-pyridyl)ethenyl]-2-naphthoate → Methyl 6-[1-(3-pyridyl)ethyl]-2-naphthoate

HRID 569797Notes

Reaction equation

HRID 569797 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[C:14]([C:19]([O:21][CH3:22])=[O:20])[CH:13]=[CH:12]3)=[CH2:8])[CH:2]=1.[H][H]>CO.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[C:14]([C:19]([O:21][CH3:22])=[O:20])[CH:13]=[CH:12]3)[CH3:8])[CH:2]=1

Participants

5

Reactant 2

HCID 20146227Methyl 6-[1-(3-pyridyl)ethenyl]-2-naphthoateHCID 178418361HCID 178418361, compound

Product 1

HCID 13687915Methyl 6-[1-(3-pyridyl)ethyl]-2-naphthoateYield 20%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

130 mg of Pd/C (10%) are added to 0.25 g (0.86 mmol) of methyl 6-[1-(3-pyridyl)ethenyl]-2-naphthoate in 25 ml of absolute methanol, and hydrogenation is carried out under atmospheric pressure (hydrogen uptake: 40 ml). The catalyst is then removed by filtration, and the solution is evaporated and chromatographed on silica gel using ethyl acetate. 50 mg (20%) of methyl 6-[1-(3-pyridyl)ethyl]-2-naphthoate are obtained as an oil. RF (ethyl acetate): 0.34.

Workup

  1. customThe catalyst is then removed by filtration
  2. customthe solution is evaporated
  3. customchromatographed on silica gel

Sources & evidence

ORD record
ord-335b4621e9214b8094b7c06d48863b27
Source dataset
uspto-grants-1988_03
Patent number
US04734406

Reaction notes

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