Hydrochloric Acid → (2,6-Dichloro-5-fluoropyridin-3-yl)methanamine

HRID 40135

Reaction equation

HRID 40135 reaction equation
Cl.[Cl:2][C:3]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:4]=1[C:5]#[N:6]>CO.[Pd]>[Cl:2][C:3]1[C:4]([CH2:5][NH2:6])=[CH:7][C:8]([F:12])=[C:9]([Cl:11])[N:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrile

Product 1

HCID 55255125(2,6-Dichloro-5-fluoropyridin-3-yl)methanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a Parr reaction bottle was added Pd—C (10%, 560 mg, 0.52 mmol), followed by 6 M HCl (50 ml) and a solution of 2,6-dichloro-5-fluoronicotinonitrile (Aldrich, 10.0 g, 52.4 mmol) in MeOH (100 ml). The mixture was placed under 50 psi H2 on a shaker type Parr apparatus for 21 h, filtered and concentrated. The crude was dissolved in EtOAc, basified with aqueous NaOH, and the layers were separated. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo to yield the title compound as crude light yellow oil. Used without further purification.

Workup

  1. customTo a Parr reaction bottle
  2. filtrationfiltered
  3. concentrationconcentrated
  4. dissolutionThe crude was dissolved in EtOAc
  5. customthe layers were separated
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f8b145b3d1e4d67813cc531a8167cc1
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Linked notes

Loading…