Hydrochloric Acid → 3-Fluoro-2-pyridinemethanamine

HRID 1059685Notes

Reaction equation

HRID 1059685 reaction equation
[C:1]([C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].Cl>C(O)C.[Pd]>[NH2:2][CH2:1][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 70604082-Cyano-3-fluoropyridine

Product 1

HCID 112057543-Fluoro-2-pyridinemethanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A stirred solution of 6.11 g (50.1 mmol) of 2-cyano-3-fluoropyridine in 250 mL of ethanol and 12.5 mL (150 mmol) of conc. HCl was hydrogenated over 1.90 g of 10% palladium on carbon at 40 psi for 16 h. The catalyst was removed by filtration and the solvents removed at reduced pressure. The resulting solid was diluted with acetonitrile and filtered to give 8.0 g of A as an off-white solid: 1H NMR (CD3OD) δ 8.48 (d, 1H, 4.8 Hz), 7.69 (td, 1H, 9.2, 1.1 Hz), 7.68 (ddd, 1H, 8.8, 4.4, 4.4 Hz), 4.34 (s, 2H).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvents removed at reduced pressure
  3. additionThe resulting solid was diluted with acetonitrile
  4. filtrationfiltered
  5. customto give 8.0 g of A as an off-white solid

Sources & evidence

ORD record
ord-62a7d1a9a1004a26b24fdf57d673780a
Source dataset
uspto-grants-2003_02
Patent number
US06521625B2

Reaction notes

Loading…