Ammonia → C-[3-(3,4-dihydro-2H-quinoline-1-yl)pyridine-2-yl]methylamine

HRID 1592466Notes

Reaction equation

HRID 1592466 reaction equation
[N:1]1([C:11]2[C:12]([C:17]#[N:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.N>[Ni].CO>[N:1]1([C:11]2[C:12]([CH2:17][NH2:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 672715793-(3,4-dihydro-2H-quinoline-1-yl)pyridine-2-carbonitrile

Product 1

HCID 67271944C-[3-(3,4-dihydro-2H-quinoline-1-yl)pyridine-2-yl]methylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney-Ni slurry (6 g) was placed in a 1 L heavy-duty hydrogenation flask under a N2 blanket. The catalyst was allowed to settle and the supernatant was removed by suction. The catalyst was washed with anhydrous MeOH (100 mL×3) by settlement and suction. Then 3-(3,4-dihydro-2H-quinoline-1-yl)pyridine-2-carbonitrile (2.35 g, 10 mmol) was added as a MeOH solution (170 mL) and the mixture was saturated with NH3 by bubbling anhydrous NH3 through the mixture for 10 minutes at room temperature. The mixture was hydrogenated at 40 psi for 4 h at room temperature on a Parr hydrogenation apparatus. The mixture was filtered through a celite pad (60 mL sintered glass fumnel, 1 cm thickness) and the filter cake was washed with MeOH (total filtrate 200 mL). The filtrate was concentrated to dryness by rotary evaporation, and the residue was purified by silica gel column chromatography (200 mL silica, 10% MeOH/CH2Cl2 containing 1% NH4OH) to give C-[3-(3,4-dihydro-2H-quinoline-1-yl)pyridine-2-yl]methylamine as a yellow oil, 2.19 g (92%).

Workup

  1. customthe supernatant was removed by suction
  2. washThe catalyst was washed with anhydrous MeOH (100 mL×3) by settlement and suction
  3. customby bubbling anhydrous NH3 through the mixture for 10 minutes at room temperature
  4. filtrationThe mixture was filtered through a celite pad (60 mL sintered glass fumnel, 1 cm thickness)
  5. washthe filter cake was washed with MeOH (total filtrate 200 mL)
  6. concentrationThe filtrate was concentrated to dryness by rotary evaporation
  7. customthe residue was purified by silica gel column chromatography (200 mL silica, 10% MeOH/CH2Cl2 containing 1% NH4OH)

Sources & evidence

ORD record
ord-4395185e6a4840de8db16ff0f15b1131
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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