Ammonia → 6-(Aminomethyl)quinoline

HRID 2041235Notes

Reaction equation

HRID 2041235 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.N>CO.[Ni]>[NH2:12][CH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2

Participants

5

Reactant 2

HCID 222AmmoniaHCID 592995Quinoline-6-carbonitrile

Product 1

HCID 15143846-(Aminomethyl)quinolineYield 78%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Combine 6-quinolinecarbonitrile (1.0 g, 6.49 mmol), Raney® 3201 nickel (slurry in water, 0.2 g), 2N ammonia in methanol (20 mL) and hydrogenate at 50 psi for 1 h. Filter the reaction mixture through a pad of Celite®, remove the solvent and purify by SCX chromatography to obtain the title compound as a yellow oil (0.8 g, 78%).

Workup

  1. filtrationFilter the reaction mixture through a pad of Celite®
  2. customremove the solvent
  3. custompurify by SCX chromatography

Sources & evidence

ORD record
ord-632efd7328244a6a9180cef835e38d7c
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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