Hydrochloric Acid → 1-(6-Fluoropyridin-2-yl)methanamine--hydrogen chloride (1/2)

HRID 911315Notes

Reaction equation

HRID 911315 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[N:4]=1)#[N:2].[ClH:10]>C(O)C.[Pd]>[ClH:10].[ClH:10].[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[N:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 142963696-Fluoropyridine-2-carbonitrile

Product 1

HCID 513420701-(6-Fluoropyridin-2-yl)methanamine--hydrogen chloride (1/2)Yield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve 2-cyano-6-fluoropyridine (300 mg, 2.46 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 to give the title compound as a solid (356 mg, 73%). MS (ES+) m/z: 127 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-f08b407447a94c8dab46589a9cf43047
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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