HCID 14434140, compound → HCID 69945910, compound

HRID 2229230Notes

Reaction equation

HRID 2229230 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](/[CH:13]=[CH:14]/[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:12]>CC(O)=O.CO.C(Cl)Cl.[Pd]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH2:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:12]

Participants

4

Reactant 1

HCID 14434140HCID 14434140, compound

Product 1

HCID 69945910HCID 69945910, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21877243DCM MeOH AcOHSolvent

Procedure

A mixture of (2-naphthyl) [(E)-2-(3-pyridyl)-1-ethenyl]ketone (5.02 g) and palladium black (0.15 g) in AcOH—MeOH—CH2Cl2 (4 ml/50 ml/20 ml) was stirred under hydrogen atmosphere at room temperature for 3 hours. The catalyst was filtered off and the filtrate was concentrated in vacuo. The residue dissolved in ethyl acetate, washed with saturated aqueous NaHCO3 solution and brine, and dried. After removal of the solvent, the residue was recrystallized from hexane-ethyl acetate to give the titled compound (3.48 g) as colorless prisms.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue dissolved in ethyl acetate
  4. washwashed with saturated aqueous NaHCO3 solution and brine
  5. customdried
  6. customAfter removal of the solvent
  7. customthe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-d933a0d9d840497b9579618d3ed0438a
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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