Hydrochloric Acid → 1-(3-Fluoropyridin-2-yl)methanamine--hydrogen chloride (1/2)

HRID 911313Notes

Reaction equation

HRID 911313 reaction equation
[C:1]([C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[ClH:10]>C(O)C.[Pd]>[ClH:10].[ClH:10].[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 186309011-(3-Fluoropyridin-2-yl)methanamine--hydrogen chloride (1/2)Yield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve 2-cyano-3-fluoropyridine (300 mg, 2.457 mmol) in absolute ethanol (12 mL). Add 10% Pd/C (93 mg) and concentrated HCl (0.614 mL, 7.37 mmol). Hydrogenate at 40 psi overnight. Filter through Celite® and concentrate in vacuo to give the title compound as a solid (440 mg, 90%). MS (ES+) m/z: 127 (M+H)+.

Workup

  1. customat 40 psi overnight
  2. filtrationFilter through Celite®
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-e362ee5439c34689abba182b2212778d
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…