Sodium Methoxide → 6-Methoxy-2-methylpyridine-3-carbonitrile

HRID 574117Notes

Reaction equation

HRID 574117 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([CH3:13])[N:6]=1>CO>[CH3:1][O:2][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([CH3:13])[N:6]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 123877376-Chloro-2-methylnicotinonitrile

Product 1

HCID 137499186-Methoxy-2-methylpyridine-3-carbonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (20 g, 0.4 mol) was added to a solution of 6-chloro-2-methylnicotinonitrile (132, 10 g, 66 mmol) in methanol (150 mL), and the mixture was heated at reflux for 1.5 h and cooled to room temperature. The precipitate was removed by filtration, and the filtrate was concentrated to dryness. The crude solid was redissolved in chloroform; and the resulting solution was filtered through a layer of silica gel, washing with extra portions of chloroform. The combined filtrates were evaporated to dryness to yield 41 (8.3 g, 87%): mp 81-82° C. (lit. (Synthesis 1991, 894-896) mp 80-80.5° C.). 1HNMR (300 MHz, CDCl3) δ 7.66 (d, J=8.5 Hz, 1H), 6.59 (d, J=8.5 Hz, 1H), 3.94 (s, 3H), 2.62 (s, 3H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1.5 h
  3. customThe precipitate was removed by filtration
  4. concentrationthe filtrate was concentrated to dryness
  5. dissolutionThe crude solid was redissolved in chloroform
  6. filtrationand the resulting solution was filtered through a layer of silica gel
  7. washwashing with extra portions of chloroform
  8. customThe combined filtrates were evaporated to dryness

Sources & evidence

ORD record
ord-563b472e7d5146a09ad5c8703d4944be
Source dataset
uspto-grants-2015_05
Patent number
US09034870B2

Reaction notes

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