Acetic Anhydride → (6-Cyano-3-methyl-2-pyridinyl)methyl acetate

HRID 2356626Notes

Reaction equation

HRID 2356626 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH3:8][C:9]1C(C)=[N+:13]([O-])[C:12]([C:17]#[N:18])=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+]>>[C:5]([O:4][CH2:1][C:2]1[C:9]([CH3:8])=[CH:10][CH:11]=[C:12]([C:17]#[N:18])[N:13]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 68455695HCID 68455695, compound

Product 1

HCID 68457478(6-Cyano-3-methyl-2-pyridinyl)methyl acetateYield 67%

Conditions

Temperature
120 °C

Procedure

To acetic anhydride (12 ml) at 120° C. was added 5,6-dimethyl-2-pyridine-carbonitrile 1-oxide (3.02 g) and the solution heated at 120° C. for 5 minutes then under reflux for 2.5 hours. After cooling the solution was added to ice (ca. 80 g) and the mixture neutralized with sodium bicarbonate. It was extracted with ether (80 ml then 2×40 ml) and the combined extracts washed with brine (40 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 (2.60 g, 67%) as a pale yellow solid. LC/MS [MH+]=191, RT=2.05 min.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. temperatureAfter cooling the solution
  3. extractionIt was extracted with ether (80 ml
  4. wash2×40 ml) and the combined extracts washed with brine (40 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by Biotage chromatography
  8. washeluting with 2:1 hexane

Sources & evidence

ORD record
ord-e3f3ca37c7db45c4af1c05e45434686f
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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