2-Chloro-4-cyanopyridine → 2-Methoxyisonicotinonitrile

HRID 1719154Notes

Reaction equation

HRID 1719154 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][O-:11].[Na+]>CO.O1CCOCC1.CO>[CH3:10][O:11][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 5686382-Chloro-4-cyanopyridineHCID 10942334Sodium Methoxide

Product 1

HCID 72048872-MethoxyisonicotinonitrileYield 110.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21966525Dioxane MethanolSolvent

Procedure

2-Chloro-4-cyanopyridine (115.53 g) in methanol/dioxan (1:1, 850 ml) was added to a solution of sodium methoxide (prepared from 20.8 g sodium) in methanol (285 ml) and the mixture was boiled under reflux for 2.5 hours and was allowed to cool. The mixture was filtered and the volume of the filtrate was reduced by evaporation to 200 ml and water (400 ml) was added. The solid which precipitated out was filtered off to give 2-methoxy-4-cyanopyridine (57.2 g, 51%) m.p. 93°-95.5°.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. temperatureto cool
  3. filtrationThe mixture was filtered
  4. customthe volume of the filtrate was reduced by evaporation to 200 ml and water (400 ml)
  5. additionwas added
  6. customThe solid which precipitated out
  7. filtrationwas filtered off

Sources & evidence

ORD record
ord-e87181f7f7d14401b5fbd820cbc58438
Source dataset
uspto-grants-1985_09
Patent number
US04539207

Reaction notes

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