Acetic Acid → HCID 18467031, compound

HRID 2229234Notes

Reaction equation

HRID 2229234 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[CH:8]/[C:9]([C:11]2[CH:20]=[CH:19][C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[CH:12]=2)=[O:10])[CH:2]=1.C(O)(=O)C>CO.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][C:9]([C:11]2[CH:20]=[CH:19][C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[CH:12]=2)=[O:10])[CH:2]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 18467015HCID 18467015, compound

Product 1

HCID 18467031HCID 18467031, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of [(E)-2-(3-pyridyl)ethenyl]-(5,6,7,8-tetrahydronaphthalen-2-yl)ketone (6.32 g), palladium black (150 mg) and acetic acid (3 ml) in MeOH (50 ml) was stirred under hydrogen atmosphere at room temperature for 6 hours. The catalyst was filtered off and the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with saturated aqueous NaHCO3 solution and brine, and dried. After removal of the solvent, the residue was recrystallized f rom hexane-ethyl acetate to give the titled compound (3.93 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was 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 f

Sources & evidence

ORD record
ord-5cbb3f16c0d146f7995e8986321f2c51
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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