Potassium Carbonate → 3-(4-Pyridinylmethoxy)benzonitrile

HRID 619192Notes

Reaction equation

HRID 619192 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1>CN(C=O)C>[N:22]1[CH:23]=[CH:24][C:19]([CH2:18][O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[C:5]#[N:6])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 745704-(Chloromethyl)pyridinium chloride

Product 1

HCID 218460893-(4-Pyridinylmethoxy)benzonitrileYield 107%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-hydroxybenzonitrile (4.76 g, 0.04 mol), K2CO3 (16.6 g, 0.12 mol) and DMF (100 ml) under argon was added 4-chloromethylpyridine hydrochloride (6.56 g, 0.04 mol). The reaction mixture was stirred at room temperature for about two days, the solvent was evaporated and the residue was partitioned between water and CH2Cl2. The organic layer was washed with 2N aqueous NaOH (1×100 ml), brine, then was dried over MgSO4. The solvent was removed in vacuo to afford, as an amber solid, 9.0 g of 3-(4-pyridinylmethoxy)benzonitrile.

Workup

  1. customthe solvent was evaporated
  2. customthe residue was partitioned between water and CH2Cl2
  3. washThe organic layer was washed with 2N aqueous NaOH (1×100 ml), brine
  4. dry with materialwas dried over MgSO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-914fe003e26b4b57ac31e3aa6aa548d6
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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