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

HRID 228496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 228496
[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+].CC(N(C)C)=O.C1(C)C=CC=CC=1>C(OCC)(=O)C>[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]

Komponenten

6

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 66603805toluene N,N-dimethylacetamide

Produkt 1

HCID 471502166-(4-Formylphenoxy)nicotinonitrileAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Combine 4-Hydroxybenzaldehyde (8.0 g, 65.5 mmol), 6-Chloronicotinonitrile (9.07 g, 65.5 mmol), powdered K2CO3 (13.6 g, 98.3 mmol), and DMA/Toluene (80/240 mL) in a 500 mL RB flask equipped with a stir, reflux condenser and a Dean Stark Trap. Reflux the reaction mixture for several hours under a Nitrogen atmosphere then cool to room temperature and quench with sat NH4Cl (aq). Add Ethyl acetate to extract the product and wash several times with water and then brine. Dry the organic layer over Na2SO4. Concentrate and flash chromatograph using 2:1 Hexanes:Ethyl acetate to give 13.2 g (88% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 7.1 (1H, d), 7.3-7.4 (2H, m), 7.9-8.0 (3H, m), 8.5 (1H, d), 10.0 (1H, s); MS m/z 225 (M+1).

Aufarbeitung

  1. temperaturereflux condenser
  2. temperatureReflux the reaction mixture for several hours under a Nitrogen atmosphere
  3. customquench with sat NH4Cl (aq)
  4. extractionAdd Ethyl acetate to extract the product
  5. washwash several times with water
  6. dry with materialDry the organic layer over Na2SO4
  7. concentrationConcentrate

Quellen und Nachweise

ORD-Eintrag
ord-9aed9d76c31741ec977db8b707c2878d
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560463B2

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