HCID 86639587, compound → HCID 67326741, compound

HRID 1910824Notes

Reaction equation

HRID 1910824 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH:9]=[CH:10][CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[N:3]=1>[Pd].CO>[CH3:8][C:6]1[CH:7]=[C:2]([CH3:1])[N:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH:5]=1

Participants

4

Reactant 1

HCID 86639587HCID 86639587, compound

Product 1

HCID 67326741HCID 67326741, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (10%, 50 mg) was added to a solution of 2,4-dimethyl-6-[4-(4-nitro-phenyl)-buta-1,3-dienyl]-pyridine (0.5 g, 1.78 mmol) in methanol (20 mL) under a nitrogen atmosphere. The reaction mixture was hydrogenated under balloon pressure for 4 h at room temperature, then filtered through celite and washed with methanol. The filtrate was evaporated under reduced pressure and the residue was washed with pentane (20 mL) to afford 4-[4-(4,6-dimethyl-pyridin-2-yl)-butyl]-phenylamine (320 mg, 71%) as a brownish pink semi-solid.

Workup

  1. filtrationfiltered through celite
  2. washwashed with methanol
  3. customThe filtrate was evaporated under reduced pressure
  4. washthe residue was washed with pentane (20 mL)

Sources & evidence

ORD record
ord-0e3dffce801a4073a781f2f51dfa2982
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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