Dichloromethane → 2-Formylisonicotinonitrile

HRID 1161130Notes

Reaction equation

HRID 1161130 reaction equation
[Se](=O)=O.[OH:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][N:13]=1)[C:9]#[N:10].ClCCl>O1CCOCC1>[CH:5]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][N:13]=1)[C:9]#[N:10])=[O:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24007Selenium DioxideHCID 132925992-(Hydroxymethyl)pyridine-4-carbonitrile

Product 1

HCID 147614682-FormylisonicotinonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Add selenium dioxide (2.69 g, 24.2 mmol) to a solution of 2-hydroxymethyl-isonicotinonitrile (5.86 g, 43.7 mmol) in dioxane (120 mL). Heat reaction to 80° C. After 4 hours, cool to room temperature. Add dichloromethane (500 mL) and celite and stir. After 15 minutes, filter through a plug of silica eluting with dichloromethane. Concentrate filtrate under reduced pressure to yield the title compound as an orange solid (5.30 g, 92%): 1H NMR (DMSO-d6) δ 8.19 (dd, 1H), 8.34 (t, 1H), 9.07 (dd, 1H), 10.01 (s, 1H).

Workup

  1. temperatureHeat
  2. customreaction to 80° C
  3. waitAfter 15 minutes
  4. filtrationfilter through a plug of silica eluting with dichloromethane

Sources & evidence

ORD record
ord-70df6af4df79492b9f4d374b1141ffc6
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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