Phosphoric Acid → 2-Formylisonicotinonitrile

HRID 854345Notes

Reaction equation

HRID 854345 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][OH:10])[CH:4]=1)#[N:2].P(=O)(O)(O)O>CS(C)=O>[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]=[O:10])[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 132925992-(Hydroxymethyl)pyridine-4-carbonitrile

Product 1

HCID 147614682-Formylisonicotinonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 4-cyano-2-hydroxymethylpyridine (1.1 g, 8.2 mmol) from stage A in dry DMSO (18 mL) was added N,N-dicyclohexylcarbodiimide (5.08 g, 24.6 mmol) and phosphoric acid (0.4 g, 4.1 mmol). The mixture was stirred overnight at room temperature. The solid was removed by filtration and washed with ether and water. The filtrate and washings were combined, and the organic layer separated. The aqueous layer was further extracted 4 times with ether, the organics combined, dried over magnesium sulphate and evaporated. The residue was purified by SPE silica column chromatography, eluting with dichloromethane, then chloroform, then diethyl ether. Evaporation of the appropriate fractions afforded 4-cyanopyridine-2-carboxaldehyde as a solid.

Workup

  1. customThe solid was removed by filtration
  2. washwashed with ether and water
  3. customthe organic layer separated
  4. extractionThe aqueous layer was further extracted 4 times with ether
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue was purified by SPE silica column chromatography
  8. washeluting with dichloromethane
  9. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-73a62004ab934714895595d51840bd01
Source dataset
uspto-grants-2007_08
Patent number
US07259163B2

Reaction notes

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