Acetic Anhydride → 6-Acetamido-3-methylpyridin-2-yl acetate

HRID 1772911Notes

Reaction equation

HRID 1772911 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][N+:6]=1[O-])(=[O:3])[CH3:2].[C:13]([O:16]C(=O)C)(=[O:15])[CH3:14]>>[C:13]([O:16][C:7]1[C:8]([CH3:11])=[CH:9][CH:10]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[N:6]=1)(=[O:15])[CH3:14]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 178474150HCID 178474150, compound

Product 1

HCID 900222806-Acetamido-3-methylpyridin-2-yl acetate

Procedure

A solution of 2-acetamido-5-methylpyridine N-oxide (28.2 g, 170 mmol) in acetic anhydride (840 mL) was stirred at 70° C. for 4 h. After cooling to rt and concentration in vacuo Et2O (180 mL) was added and the resulting solids isolated by filtration and washed with MeOH to give 6-acetamido-3-methylpyridin-2-yl acetate (6.87 g, 33.0 mmol) as a pale brown solid.

Workup

  1. concentrationconcentration in vacuo Et2O (180 mL)
  2. additionwas added
  3. customthe resulting solids isolated by filtration
  4. washwashed with MeOH

Sources & evidence

ORD record
ord-d7be98419ac840d8b0ef9f9bfd6e41ac
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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