2-Vinylpyridine → N-Ethylpyridin-4-amine

HRID 1458951Notes

Reaction equation

HRID 1458951 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)=[CH2:2].[Cl-].[NH4+:10].[OH-].[Na+]>CO.O>[N:10]1[CH:7]=[CH:8][C:3]([NH:4][CH2:5][CH3:6])=[CH:1][CH:2]=1

Participants

5

Reactant 3

HCID 75212-VinylpyridineHCID 14798Sodium HydroxideHCID 25517Ammonium Chloride

Product 1

HCID 12661197N-Ethylpyridin-4-amine

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A slurry of vinyl pyridine (161.4 mL, 1.5 mol) and ammonium chloride (240.7 g, 4.5 mol) in 1:1 MeOH/H2O (1.2 L) was heated to reflux for 18 h. The resulting homogenous solution was basified to pH13 with 3N NaOH and extracted repeatedly with CH2Cl2. The organic extracts were combined and concentrated to give a green oil, which was fractionally distilled to give 2-1 as an amber liquid.

Workup

  1. temperatureto reflux for 18 h
  2. extractionextracted repeatedly with CH2Cl2
  3. concentrationconcentrated
  4. customto give a green oil, which
  5. distillationwas fractionally distilled

Sources & evidence

ORD record
ord-6e3c1c1c2a09487daa176db3e6ad279c
Source dataset
uspto-grants-1998_12
Patent number
US05852045

Reaction notes

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