4-[2-(4-Nitro-phenyl)-vinyl]-pyridine → 4-[2-(Pyridin-4-yl)ethyl]aniline

HRID 588027

Reaction equation

HRID 588027 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CCOC(C)=O>[N:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 3071364-[2-(4-Nitro-phenyl)-vinyl]-pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 2332884-[2-(Pyridin-4-yl)ethyl]anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To the EtOAc solution (30 mL) of 4-[2-(4-nitro-phenyl)-vinyl]-pyridine (160 mg, 0.71 mmol) was added palladium on carbon (0.1 g, 50% wet). The suspension was hydrogenated at 50 psi of hydrogen for 2 hours. The mixture was filtered over a celite pad. The filtrate was concentrate to give 4-(2-pyridin-4-yl-ethyl)-phenylamine as a yellow solid (140 mg, 100%).

Workup

  1. filtrationThe mixture was filtered over a celite pad
  2. concentrationThe filtrate was concentrate

Sources & evidence

ORD record
ord-fbf0b7d100a3482ead33531dc2780fe1
Source dataset
uspto-grants-2016_01
Patent number
US09227954B2

Linked notes

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