Water → 2-(2,4-Dichloro-phenyl)-3-(6-methoxy-pyridin-3-yl)-3-oxo-propionitrile

HRID 333861

Reaktionsgleichung

Reaktionsgleichung von HRID 333861
CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[N:6][CH:5]=1.[Cl:13][C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=1[CH2:16][C:17]#[N:18].O>C(O)(C)(C)C>[Cl:13][C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=1[CH:16]([C:3]([C:4]1[CH:5]=[N:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=1)=[O:12])[C:17]#[N:18]

Komponenten

5

Edukt 3

HCID 962WaterHCID 805662,4-DichlorophenylacetonitrileHCID 586039Methyl 6-methoxypyridine-3-carboxylate

Produkt 1

HCID 668131162-(2,4-Dichloro-phenyl)-3-(6-methoxy-pyridin-3-yl)-3-oxo-propionitrileAusbeute 29,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of potassium-tert-butylate (2.052 g) in tert-butanol (25 ml) was added methyl-6-methoxynicotinate (2.5 g). 2,4-Dichlorobenzyl cyanide (2.782 g) was added portion wise. The mixture was heated to 100° C. for 1.5 h. After cooling to room temperature, water (100 ml) was added and the mixture was washed with diethyl ether. The aqueous phase was neutralized with concentrated aqueous HCl and extracted with EtOAc. The organic phase was washed with water and with brine, dried (MgSO4), filtered and concentrated to dryness to give the title compound (1.407 g) as a yellow foam that was used in the next step without further purification. MS (m/e)=321.0 [M+H+].

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washthe mixture was washed with diethyl ether
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water and with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-9dcae863c2d24463ae9abf9130636ceb
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883786B2

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