3-Hydroxypyridine → 2-(Pyridin-3-yloxy)acetonitrile

HRID 56268Notes

Reaction equation

HRID 56268 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([OH:7])[CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:15][C:16]#[N:17]>CC#N>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:15][C:16]#[N:17])[CH:2]=1

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 11430Potassium CarbonateHCID 11534Bromoacetonitrile

Product 1

HCID 199146182-(Pyridin-3-yloxy)acetonitrileYield 16%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of pyridin-3-ol (4.0 g, 42.1 mmol) and K2CO3 (6.96 g, 50.4 mmol) in CH3CN (6 mL) was added dropwise 2-bromoacetonitrile (2.52 g, 21.0 mmol) at rt and the mixture was stirred at rt for 40 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as a yellow solid (0.45 g, 16%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

Sources & evidence

ORD record
ord-bf1779f436194aab9f739c5a14f10a16
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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