Ammonia → (2-Methoxypyridin-4-yl)methanamine

HRID 711262

Reaction equation

HRID 711262 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][N:10]=1)[C:6]#[N:7].N>CO.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][NH2:7])[CH:8]=[CH:9][N:10]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 72048872-Methoxyisonicotinonitrile

Product 1

HCID 16227983(2-Methoxypyridin-4-yl)methanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To the solution of 2-methoxyisonicotinonitrile 56-1 (1.1 g, 8.2 mmol) in methanol with 7 N NH3 was added Raney-Nickel (1.0 g). The reaction was shaken under H2 at 50 psi at room temperature in Parr shaker for 12 hours. The Raney-Nickel was removed by rotary evaporation and the filtrate was taken to dryness by rotary evaporation to give crude (2-methoxypyridin-4-yl)methanamine 56-2. MS m/z 139.2 (M+1).

Workup

  1. customThe Raney-Nickel was removed by rotary evaporation
  2. customthe filtrate was taken to dryness by rotary evaporation

Sources & evidence

ORD record
ord-789e41ddbe0f464da7f794949dfd6c7c
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Linked notes

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