Pyridine → 2-Methyl-3-(pyridin-3-yl)benzonitrile

HRID 2295865Notes

Reaction equation

HRID 2295865 reaction equation
Cl[C:2]1[C:3]([CH3:14])=[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[C-]#N.[N:17]1C=CC=C[CH:18]=1.[OH-].[NH4+]>[Cu].C(Cl)Cl>[C:18]([C:2]1[C:3]([CH3:14])=[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1)#[N:17]

Participants

7

Reactant 4

HCID 1049PyridineHCID 5975CyanideHCID 14923Ammonium HydroxideHCID 13245930HCID 13245930, compound

Product 1

HCID 132459322-Methyl-3-(pyridin-3-yl)benzonitrileYield 85.8%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
195 °C

Procedure

A mixture of 7.5 g (0.012 mol) of 3-(3-chloro-2-methylphenyl)pyridine and 1.7 g (0.018 mol) of copper I cyanide in 1.45 g (0.018 mol) of pyridine was heated at 195° C. for 18 hours. The reaction mixture was cooled to 50° C., and 40 mL of methylene chloride was added with stirring. The mixture was placed in a separatory funnel, and 75 mL of methylene chloride and 75 mL of a 35% aqueous solution of ammonium hydroxide were added. The mixture was shaken for five minutes, then passed through a fiber glass filter paper. The layers were separated, and the aqueous layer was washed with two portions of 40 mL each of methylene chloride. The combined organic layers were washed with three portions of 40 mL each of a 35% aqueous solution of ammonium hydroxide. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give 2.0 g of 3 -(3-cyano-2-methylphenyl)pyridine.

Workup

  1. temperatureThe reaction mixture was cooled to 50° C.
  2. customThe mixture was placed in a separatory funnel
  3. stirringThe mixture was shaken for five minutes
  4. filtrationfilter paper
  5. customThe layers were separated
  6. washthe aqueous layer was washed with two portions of 40 mL each of methylene chloride
  7. washThe combined organic layers were washed with three portions of 40 mL each of a 35% aqueous solution of ammonium hydroxide
  8. dry with materialThe organic layer was dried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-97e17a5817614766aae1885e1031ad4d
Source dataset
uspto-grants-1984_01
Patent number
US04426524

Reaction notes

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