Methanol → 2-Methoxypyridine-3-carbonitrile

HRID 1048743

Reaction equation

HRID 1048743 reaction equation
[Na].[CH3:2][OH:3].Cl[C:5]1[N:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8]>O>[CH3:2][O:3][C:5]1[N:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 810792-ChloronicotinonitrileHCID 5360545Sodium

Product 1

HCID 2520992-Methoxypyridine-3-carbonitrileYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.98 g (217 mmol) of sodium is added to 80 ml of anhydrous methanol. The reaction medium is stirred at room temperature for 10 minutes and then 10 g (72.2 mmol) of 2-chloronicotinonitrile is added at 0° C. The reaction medium is stirred at 25° C. for 16 hours. The reaction is hydrolyzed by slowly adding water at 0° C. After returning to room temperature, the precipitate obtained is filtered, rinsed with water and then dried at 50° C. to yield 7.85 g (81%) of 2-methoxy-nicotinonitrile in the form of a yellow solid.

Workup

  1. stirringThe reaction medium is stirred at 25° C. for 16 hours
  2. customAfter returning to room temperature
  3. customthe precipitate obtained
  4. filtrationis filtered
  5. washrinsed with water
  6. customdried at 50° C.

Sources & evidence

ORD record
ord-92c99cd601214552a04f44e26321ed1b
Source dataset
uspto-grants-2016_07
Patent number
US09381195B2

Linked notes

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