4-Vinylpyridine → 4-Pyridineethanamine

HRID 399438Notes

Reaction equation

HRID 399438 reaction equation
[NH4+:1].[Cl-].[CH:3]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)=[CH2:4].[OH-].[Na+]>O>[N:8]1[CH:9]=[CH:10][C:5]([CH2:3][CH2:4][NH2:1])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 75024-VinylpyridineHCID 14798Sodium HydroxideHCID 25517Ammonium Chloride

Product 1

HCID 832754-Pyridineethanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of NH4Cl in 200 ml of H2O was placed in a 1L Flask. 4-Vinyl pyridine (56.4 ml, 0.52 mol) was added along with 150 ml CH3 OH and on the mixture heated at 60° for 18 h. The reaction solution was cooled to 0° in an ice bath and made basic by the addition of 30% NaOH. The basic solution was extracted with CH2Cl2 (5×100 ml) and the pooled extracts dried, then evaporated. Vacuum distillation of the residue afforded 12-1 as a colorless liquid.

Workup

  1. temperatureheated at 60° for 18 h
  2. temperatureThe reaction solution was cooled to 0° in an ice bath
  3. extractionThe basic solution was extracted with CH2Cl2 (5×100 ml)
  4. customthe pooled extracts dried
  5. customevaporated
  6. distillationVacuum distillation of the residue

Sources & evidence

ORD record
ord-73e93d244811459fb0778c010ca0c42f
Source dataset
uspto-grants-1998_10
Patent number
US05821241

Reaction notes

Loading…