Acetic Anhydride → (6-Cyano-5-methyl-2-pyridinyl)methyl acetate

HRID 2356632Notes

Reaction equation

HRID 2356632 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[N+:4]([O-])[C:3]=1[C:10]#[N:11].C(=O)(O)[O-].[Na+].[C:17]([O:20]C(=O)C)(=[O:19])[CH3:18]>>[C:17]([O:20][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([C:10]#[N:11])[N:4]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 684559153,6-Dimethyl-2-pyridinecarbonitrile 1-oxide

Product 1

HCID 68457380(6-Cyano-5-methyl-2-pyridinyl)methyl acetateYield 67%

Procedure

To acetic anhydride (20 ml) at 120° was added 3,6-dimethyl-2-pyridine-carbonitrile 1-oxide (5.28 g) and the solution heated at 120° for 5 minutes then under reflux for 2 hours. After cooling the solution was added to ice (ca. 150 g) and the mixture neutralized with sodium bicarbonate. It was extracted with ether (170 ml then 2×75 ml) and the combined extracts washed with brine (60 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by Biotage chromatography eluting with 2:1 hexane:ethyl acetate to afford the title compound (3.62 g, 67%) as a pale yellow oil

Workup

  1. temperaturethe solution heated at 120° for 5 minutes
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling the solution
  4. extractionIt was extracted with ether (170 ml
  5. wash2×75 ml) and the combined extracts washed with brine (60 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by Biotage chromatography
  9. washeluting with 2:1 hexane

Sources & evidence

ORD record
ord-9189746fd8034b908e21cf2d2abd01a8
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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