2-Cyano-3-fluoropyridine → 3-Fluoro-2-pyridinemethanamine

HRID 887639Notes

Reaction equation

HRID 887639 reaction equation
[F:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1>CO.Cl.[Pd]>[F:1][C:2]1[C:3]([CH2:8][NH2:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 70604082-Cyano-3-fluoropyridine

Product 1

HCID 112057543-Fluoro-2-pyridinemethanamineYield 15.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

The mixture of 3-fluoro-pyridine-2-carbonitrile (0.81 g, 6.63 mmol) and Pd/C (0.20 g, 10% wt) in 10 ml of MeOH and 2.7 ml of concentrated HCl was placed under H2 which was provided by a balloon and stirred at RT for 4 h, filtered through Celite®, condensed, the residue was purified by flash column chromatography, 0.13 g of the titled compound was obtained as a light yellowish oil. MS (ES+): 127.1 (M+H)+. Calc'd for C6H7FN2—126.13.

Workup

  1. customwas provided by a balloon
  2. filtrationfiltered through Celite®, condensed
  3. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-e964912952914c7eaaff3987d6c3e2ba
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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