Phenol → HCID 1484343, compound

HRID 2407827Notes

Reaction equation

HRID 2407827 reaction equation
Cl[C:2]1[N:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[Cs+].[Cs+].[C:18]1([OH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(N(C)C)=O.O>[CH3:11][O:10][C:6]1[C:3]([C:4]#[N:5])=[C:2]([O:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 14709302-Chloro-4-methoxynicotinonitrile

Product 1

HCID 1484343HCID 1484343, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 2-chloro-4-methoxynicotinonitrile (1.02 g) in dimethylacetamide (30 mL) was treated with cesium carbonate (2.96 g) followed by phenol (0.683 g) at room temperature. The mixture was heated to 75° C. overnight. The mixture was cooled to room temperature, diluted with water (100 mL) and the precipitated solids collected by filtration, to provide the title compound (0.964 g) with the following physical data.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationthe precipitated solids collected by filtration

Sources & evidence

ORD record
ord-8d5421dd4a6348a785c1ad852bfeac4f
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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