1-(5-(Prop-1-en-2-yl)pyridin-3-yl)ethanone oxime → 1-[5-(Propan-2-yl)pyridin-3-yl]ethan-1-amine

HRID 2071021Notes

Reaction equation

HRID 2071021 reaction equation
[CH2:1]=[C:2]([C:4]1[CH:5]=[C:6]([C:10](=[N:12]O)[CH3:11])[CH:7]=[N:8][CH:9]=1)[CH3:3]>CO.Cl.[Pd]>[CH:2]([C:4]1[CH:5]=[C:6]([CH:10]([NH2:12])[CH3:11])[CH:7]=[N:8][CH:9]=1)([CH3:3])[CH3:1]

Participants

4

Reactant 1

HCID 866474221-(5-(Prop-1-en-2-yl)pyridin-3-yl)ethanone oxime

Product 1

HCID 595701211-[5-(Propan-2-yl)pyridin-3-yl]ethan-1-amineYield 41.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21893726Hydrochloride methanolSolvent

Procedure

To a stirred solution of 1-(5-(prop-1-en-2-yl)pyridin-3-yl)ethanone oxime (400 mg) in MeOH.HCl (1.25M, 8 mL) was added 10% Pd/C (40 mg) and stirred under hydrogen atmosphere for 4 h. The catalyst was filtered off and the residue was dissolved in 5 mL of 25% aqueous NH3 and extracted with CHCl3 and the organic layer was washed with brine, dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (10% MeOH/90% CHCl3 spiked with 0.25% of Et3N) to provide 155 mg of the product.

Workup

  1. filtrationThe catalyst was filtered off
  2. dissolutionthe residue was dissolved in 5 mL of 25% aqueous NH3
  3. extractionextracted with CHCl3
  4. washthe organic layer was washed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (10% MeOH/90% CHCl3 spiked with 0.25% of Et3N)

Sources & evidence

ORD record
ord-9eaf987fd91d4b9c82df27cf8d3559d9
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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