Ethanol → HCID 86636450, compound

HRID 1483723Notes

Reaction equation

HRID 1483723 reaction equation
[CH3:1][CH2:2][O-:3].[Na+].[CH2:5]([OH:7])[CH3:6].[Cl:8][C:9]1[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11]([Cl:17])[CH:10]=1>CN(C)C=O.O>[Cl:17][C:11]1[CH:10]=[C:9]([O:3][CH2:2][CH3:1])[C:14]([C:15]#[N:16])=[CH:13][N:12]=1.[Cl:8][C:9]1[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11]([O:7][CH2:5][CH3:6])[CH:10]=1

Participants

7

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 455880804,6-Dichloropyridine-3-carbonitrile

Product 2

HCID 67441217HCID 67441217, compoundYield 6%HCID 86636450HCID 86636450, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of NaOEt in ethanol (1.93M, 18.8 mL, 36.3 mmol) was added over 10 minutes to a solution of 4,6-dichloro-nicotinonitrile (6.29 g, 36.3 mmol) in dimethylformamide (60 mL) at room temperature. The reaction was stirred for 3 hours, diluted with water (600 mL) and extracted with EtOAc (4×400 mL). The organic extracts were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash column chromatography (20% ethyl acetate/hexanes) to give the title compound as a white solid (3.82 g, 58%) and 4-chloro-6-ethoxy-nicotinonitrile (0.41 g, 6.0%) as a white solid.

Workup

  1. extractionextracted with EtOAc (4×400 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash column chromatography (20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9ff918317e4e47f4827857c6975937e1
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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