Ammonia → 5-Methyl-3-(trifluoromethyl)-2-pyridinemethanamine

HRID 251063Notes

Reaction equation

HRID 251063 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([C:10]([F:13])([F:12])[F:11])=[CH:4][C:3]=1[CH3:14].N>CO.[Ni]>[CH3:14][C:3]1[CH:4]=[C:5]([C:10]([F:13])([F:11])[F:12])[C:6]([CH2:8][NH2:9])=[N:7][CH:2]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 58997212HCID 58997212, compound

Product 1

HCID 672725865-Methyl-3-(trifluoromethyl)-2-pyridinemethanamineYield 44%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 6-chloro-5-methyl-3-trifluoromethyl-pyridine-2-carbonitrile (0.300 g, 1.36 mmol) in MeOH (5 mL) was added to a flask charged with Raney Ni (pre-washed with methanol) (˜0.6 g) in MeOH (5 mL). After saturated with NH3 gas the mixture was shaken under H2 (40 psi) for 2 h. The reaction mixture was then filtered through a celite cake, and the filtrate was concentrated by evaporation under vacuum. The residue was purified by flash chromatography on a silica gel column (200:10:1 CH2Cl2/MeOH/NH4OH), affording C-(5-methyl-3-trifluoromethyl-pyridin-2-yl)-methylamine as a colorless oil (0.113 g, 44%). 1H NMR (CDCl3) δ 2.39 (s, 3H), 4.07 (s, 2H), 7.71 (s, 1H), 8.56 (s, 1H).

Workup

  1. filtrationThe reaction mixture was then filtered through a celite cake
  2. concentrationthe filtrate was concentrated by evaporation under vacuum
  3. customThe residue was purified by flash chromatography on a silica gel column (200:10:1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-d61883382ef34587856ccf7b69bf3f37
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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