Potassium Carbonate → 3-(4-Pyridinylmethoxy)benzonitrile

HRID 1597886Notes

Reaction equation

HRID 1597886 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 CH2 Cl2. 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 CH2 Cl2
  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-705b808bfa3243039781d9523285ff33
Source dataset
uspto-grants-1998_04
Patent number
US05736548

Reaction notes

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