5-(1-Azidoethyl)-2-fluoropyridine → 6-Fluoro-α-methyl-3-pyridinemethanamine

HRID 1640875Notes

Reaction equation

HRID 1640875 reaction equation
[N:1]([CH:4]([C:6]1[CH:7]=[CH:8][C:9]([F:12])=[N:10][CH:11]=1)[CH3:5])=[N+]=[N-]>C(O)C.O=[Pt]=O>[F:12][C:9]1[N:10]=[CH:11][C:6]([CH:4]([NH2:1])[CH3:5])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 866404925-(1-Azidoethyl)-2-fluoropyridine

Product 1

HCID 586290066-Fluoro-α-methyl-3-pyridinemethanamineYield 91.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

Hydrogenate 5-(1-azido-ethyl)-2-fluoro-pyridine (4.09 g, 24.59 mmol) under a 60 psi pressure in ethanol (200 mL) in the presence of PtO2 (6% w/w). Filter the mixture after 4 h, remove the solvent on a rotovap, and dry the resulting oil under vacuum to obtain the title compound (3.15 g). GCMS m/z 140 [M]+.

Workup

  1. filtrationFilter the mixture after 4 h
  2. customremove the solvent on a rotovap
  3. customdry the resulting oil under vacuum

Sources & evidence

ORD record
ord-8a8efd6e6e8241f6ab3a4caa347f20fb
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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