HCID 2728499, compound → HCID 83486524, compound

HRID 1501123Notes

Reaction equation

HRID 1501123 reaction equation
[CH3:1][O:2][C:3]1[N:10]=[C:9]([CH3:11])[CH:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[C:4]=1[C:5]#[N:6]>C(O)C.O.NN.[Ni]>[CH3:1][O:2][C:3]1[C:4]([CH2:5][NH2:6])=[C:7]([C:12]([F:15])([F:13])[F:14])[CH:8]=[C:9]([CH3:11])[N:10]=1

Participants

6

Reactant 1

HCID 2728499HCID 2728499, compound

Product 1

HCID 83486524HCID 83486524, compoundYield 79.1%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 9321HydrazineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-methoxy-6-methyl-4-(trifluoromethyl)nicotinonitrile (0.6 g, 2.7 mmol) in ethanol (50 mL) was added the suspension of raney-Ni in water (1 mL) and hydrazine (5 mL). After stirring at 60° C. for 3 hours, the mixture was filtered and concentrated to give a residue. The residue was purified by chromatography (dichloromethane/methanol=10:1) to give (2-methoxy-6-methyl-4-(trifluoromethyl)pyridin-3-yl)methanamine (0.47 g, 77%) and used directly in next step without further purification. LRMS (M+H) m/z: calcd 220.08. found 220.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated
  3. customto give a residue
  4. customThe residue was purified by chromatography (dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-9f6ab0cbdc564c54b7c4059f88b39a81
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

Loading…