Acetic Anhydride → 3-(Acetamidomethyl)pyridine

HRID 247924Notes

Reaction equation

HRID 247924 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][NH:1][C:9](=[O:11])[CH3:10])[CH:4]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 310183-Pyridinemethanamine

Product 1

HCID 27352253-(Acetamidomethyl)pyridine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

The title compound is prepared by the procedure of Example 12 using 50 g of 3-(aminomethyl)pyridine, 50.2 ml of acetic anhydride, 2.26 g of 4-dimethylaminopyridine and 150 ml of pyridine without heating at reflux. The residue is purified by column chromatography (silica gel:20% methyl alcohol/ethyl acetate) to give 31.8 g of the desired product as a yellow oil.

Workup

  1. temperaturewithout heating
  2. temperatureat reflux
  3. customThe residue is purified by column chromatography (silica gel:20% methyl alcohol/ethyl acetate)

Sources & evidence

ORD record
ord-9c4750ba11854a57bec17790b9b6df05
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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