Ammonium Hydroxide → 2-(Pyridin-3-yl)ethan-1-amine

HRID 931518Notes

Reaction equation

HRID 931518 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]#[N:9])[CH:2]=1.[OH-].[NH4+].[H][H]>[Ni].CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][NH2:9])[CH:2]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 809233-PyridineacetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 8540512-(Pyridin-3-yl)ethan-1-amineYield 90.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(pyridin-3-yl)acetonitrile (1 g, 8.47 mmol, 1.00 equiv), Raney nickel (1 g, 17.24 mmol, 1.00 equiv) and ammonium hydroxide (3 mL) in methanol (15 mL) was stirred under 1 atmosphere of hydrogen at room temperature overnight. The catalyst was removed by filtration through a pad of Celite and washed with several portions of methanol. The filtrate and washings were combined and concentrated under vacuum to give 940 mg (45%) of 2-(pyridin-3-yl)ethanamine as a yellow oil. LC-MS: (ES, m/z): 164 [M+CH3CN+H]+, 123 [M+H]+, 106.

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite
  2. washwashed with several portions of methanol
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-03f68c0eadfd465bb8c56070eae1f903
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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