Ammonia → Pyridine, 2-methyl-3-(2-pyrrolidinyl)-

HRID 262953Notes

Reaction equation

HRID 262953 reaction equation
[C:1]([CH2:3][CH2:4][C:5]([C:7]1[C:8]([CH3:13])=[N:9][CH:10]=[CH:11][CH:12]=1)=O)#[N:2].N>C(O)C.[Ni]>[CH3:13][C:8]1[N:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH:5]1[NH:2][CH2:1][CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 122824282-Methyl-3-pyridyl 2-cyanoethyl ketone

Product 1

HCID 3053190Pyridine, 2-methyl-3-(2-pyrrolidinyl)-Yield 75%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3.15 g 2-methyl-3-pyridyl 2-cyanoethyl ketone (Preparation III) in 180 ml of ethanol saturated with ammonia was added 20 g of freshly prepared Raney nickel. The mixture was hydrogenated in a Parr apparatus at about 50 psi for 15 h. The reaction mixture was filtered to remove the catalyst and concentrated under reduced pressure. The residue was taken up in hexane and dried over Drierite. After filtration and removal of the solvent the residue was distilled. The fraction boiling at 100°-105°/0.175 mm Hg, was collected to give 2.1 g (75%) of 2-methylnornicotine.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationconcentrated under reduced pressure
  4. dry with materialdried over Drierite
  5. filtrationAfter filtration and removal of the solvent the residue
  6. distillationwas distilled
  7. customThe fraction boiling at 100°-105°/0.175 mm Hg, was collected

Sources & evidence

ORD record
ord-bb1ecf150e084331b268f32f8696ce80
Source dataset
uspto-grants-1979_05
Patent number
US04155909

Reaction notes

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