Pyridine → N-(pyridin-2-ylmethyl)acetamide

HRID 1728798Notes

Reaction equation

HRID 1728798 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.O>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][NH:1][C:9](=[O:11])[CH3:10]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 195092-Pyridinemethanamine

Product 1

HCID 5084090N-(pyridin-2-ylmethyl)acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 5.0 g 2-(aminomethyl)pyridine, 5.02 ml acetic anhydride, 0.847 g 4-dimethylaminopyridine and 35 ml of pyridine is heated at reflux temperature for 23.5 hours. The cooled solution is poured into water and extracted with methylene chloride. The organic layer is washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:5% methyl alcohol/ethyl acetate) to give 3.3 g of desired product as a light yellow oil.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 23.5 hours
  3. extractionextracted with methylene chloride
  4. washThe organic layer is washed with saturated sodium chloride
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by column chromatography (silica gel:5% methyl alcohol/ethyl acetate)

Sources & evidence

ORD record
ord-75ac4bcbc0b1432fb2f424dad63cd064
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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