Acetic Anhydride → N-[(6-Methoxypyridin-2-yl)methyl]acetamide

HRID 2413339Notes

Reaction equation

HRID 2413339 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[N:4]=1)#[N:2].[C:11]([O-])(=[O:13])[CH3:12].[Na+].C(OC(=O)C)(=O)C>[Ni]>[C:11]([NH:2][CH2:1][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[N:4]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 130236446-Methoxy-2-pyridinecarbonitrile

Product 1

HCID 13882972N-[(6-Methoxypyridin-2-yl)methyl]acetamide

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of 1.0 g (7.46 mmole) of 2-cyano-6-methoxypyridine, 0.37 g (4.48 mmole) of sodium acetate, 25 ml of acetic anhydride and about 1.0 g of Raney nickel was hydrogenated on a Paar apparatus for about 5.5 hours. The mixture was filtered, and then evaporated with warming in vacuo to provide 2-acetamidomethyl-6-methoxypyridine. The structural assignment was supported by infrared spectral analysis.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. temperaturewith warming in vacuo

Sources & evidence

ORD record
ord-cea411d96ef44adeaccb6638cf40a573
Source dataset
uspto-grants-1985_01
Patent number
US04496734

Reaction notes

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