Methylamine → 6-(Methylamino)pyridine-3-carbonitrile

HRID 990723Notes

Reaction equation

HRID 990723 reaction equation
[CH3:1][NH2:2].Cl[C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][N:5]=1>CN(C=O)C>[CH3:1][NH:2][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 178608996-(Methylamino)pyridine-3-carbonitrileYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Methylamine was bubbled into a solution of 6-chloronicotinonitrile (2 g, 14.4 mmol) in DMF (150 mL) at room temperature for 4 min. The reaction mixture was then stirred at 50° C. for 1 hour. The DMF was removed under reduced pressure. The residue was taken up in water and extracted with diethyl ether. The organic layer was washed with water and dried over Na2SO4. The solvent was evaporated in vacuo to give the title compound as a white solid (1.9 g, 99%). 1H NMR (250 MHZ, CDCl3) δ(ppm):8.3 (d, 1H); 7.55 (dd, 1H); 6.35 (d, 1H); 5.4 (brd, 1H); 2.9 (d,3H).

Workup

  1. customThe DMF was removed under reduced pressure
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-ea464ba5fcec47199035eb9a98a6dcb3
Source dataset
uspto-grants-2002_10
Patent number
US06462047B1

Reaction notes

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