2-Chloro-4-cyanopyridine → 2-Methoxyisonicotinonitrile

HRID 903348Notes

Reaction equation

HRID 903348 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>[CH3:10][O:11][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 5686382-Chloro-4-cyanopyridineHCID 10942334Sodium Methoxide

Product 1

HCID 72048872-MethoxyisonicotinonitrileYield 110.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-4-cyanopyridine (115.5 g) in methanoldioxan (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 heated under reflux for 2.5 hours and then 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 was filtered off to give 2-methoxy-4-cyanopyridine (57.2 g, 51%), m.p. 93°-95.5°.

Workup

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

Sources & evidence

ORD record
ord-3a095a42f3a34656a2b2a974efcf7502
Source dataset
uspto-grants-1980_10
Patent number
US04227000

Reaction notes

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