3-Cyano-2,6-dichloro-4-methylpyridine → 4-Methyl-3-cyanopyridine

HRID 1723015Notes

Reaction equation

HRID 1723015 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[C:4](Cl)[N:3]=1.C([O-])(=O)C.[Na+]>CO.[Pd](Cl)Cl>[C:8]([C:7]1[CH:2]=[N:3][CH:4]=[CH:5][C:6]=1[CH3:10])#[N:9]

Participants

5

Reactant 2

HCID 701313-Cyano-2,6-dichloro-4-methylpyridineHCID 517045Sodium Acetate

Product 1

HCID 2278064-Methyl-3-cyanopyridine

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2,6-dichloro-3-cyano-4-methylpyridine (47 g, 0.25 mol), sodium acetate (41.2 g, 0.5 mol), and palladium (II) chloride (0.5 g) in 220 mL of methanol was hydrogenated on a Parr apparatus under 50 PSI (initial pressure). When the uptake ceased the catalyst was filtered (solka floc) and the filtrate concentrated in vacuo. The crude residue was distilled under vacuum through a Vigreaux column and the product collected at 68°-72° C./2 mm (25.3 g, 85%, as a clear liquid).

Workup

  1. filtrationwas filtered (solka floc)
  2. concentrationthe filtrate concentrated in vacuo
  3. distillationThe crude residue was distilled under vacuum through a Vigreaux column
  4. customthe product collected at 68°-72° C./2 mm (25.3 g, 85%

Sources & evidence

ORD record
ord-743036d1f3734b5e833267f113aab653
Source dataset
uspto-grants-1989_08
Patent number
US04859671

Reaction notes

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