4-Hydroxybenzaldehyde → 6-(4-Formylphenoxy)nicotinonitrile

HRID 2219787Notes

Reaction equation

HRID 2219787 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][N:12]=2)=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 471502166-(4-Formylphenoxy)nicotinonitrileYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 4-hydroxy-benzaldehyde (1 equiv), 6-chloro-nicotinonitrile (1 equiv), and potassium carbonate (1.5 equiv) in dimethylformamide (0.1 M) and warm to 130° C. with stirring. After 3 h, cool to ambient temperature, dilute reaction mixture with water and extract with ethyl acetate (3×). Wash combined organic extracts with water and brine successively, dry over anhydrous magnesium sulfate, filter, and concentrate. Purify the residue by silica gel chromatography (hexanes:ethyl acetate 6:4) to provide the title compound as a white solid.

Workup

  1. additiondilute
  2. extractionextract with ethyl acetate (3×)
  3. washWash
  4. dry with materialdry over anhydrous magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue by silica gel chromatography (hexanes:ethyl acetate 6:4)

Sources & evidence

ORD record
ord-34b13c9c14854071aa4979f68c67a632
Source dataset
uspto-grants-2008_08
Patent number
US07414132B2

Reaction notes

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