Water → 2-Formylnicotinonitrile

HRID 7154

Reaction equation

HRID 7154 reaction equation
[C:1]([C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].O.[Se](=O)=[O:12]>O1CCOCC1>[C:1]([C:3]1[C:4]([CH:9]=[O:12])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24007Selenium DioxideHCID 47383082-Methylpyridine-3-carbonitrile

Product 1

HCID 190294752-FormylnicotinonitrileYield 10%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-cyano-2-picoline (166 mg, 1.41 mmol) in dioxane (3 mL) was added water (0.2 mL) and selenium(IV) oxide (228 mg, 2.05 mmol) and the mixture stirred at reflux overnight. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (Hexanes/ether, 3:1 then 1:1) to afford the title compound (18 mg, 10%) as a pale yellow solid. 1H NMR (CDCl3): δ 7.69 (dd, 1H, J=9, 6 Hz), 8.20 (d, 1H, J=9 Hz), 9.00 (d, 1H, J=3 Hz), 10.13 (s, 1H).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by column chromatography on silica gel (Hexanes/ether, 3:1

Sources & evidence

ORD record
ord-c91b9e7b100246bd91748a1ae525db65
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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