Hydrochloric Acid → 2-(2-Methoxybenzoyl)-3-methylpyridine

HRID 892508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 892508
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[Mg].[C:11]([C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N:14]=1)#N.Cl.[OH-:21].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:19][C:18]1[C:13]([C:11]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH3:9])=[O:21])=[N:14][CH:15]=[CH:16][CH:17]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 113582-BromoanisoleHCID 14798Sodium HydroxideHCID 8199283-Methylpyridine-2-carbonitrileHCID 5462224Magnesium

Produkt 1

HCID 198956902-(2-Methoxybenzoyl)-3-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

35.5 g of o-bromoanisole were added dropwise to 5.71 g of magnesium turnings covered with 50 ml of tetrahydrofuran while heating to maintain reflux. 15 minutes after completion of the addition 14.93 g of 2-cyano-3-methylpyridine in 150 ml of tetrahydrofuran were added dropwise without further heating. After 1 hour at room temperature dilute hydrochloric acid and ethyl acetate were added followed by dilute sodium hydroxide solution to pH 14. The mixture was extracted with ethyl acetate, the organic extract was dried over sodium sulphate and then evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:3) and then ethyl acetate/petroleum ether (1:2) for the elution. There were obtained 9.81 g of 2-methoxyphenyl 3-methyl-2-pyridyl ketone in the form of a solid of melting point 98°-100° C.

Aufarbeitung

  1. temperaturewhile heating
  2. temperatureto maintain
  3. temperaturereflux
  4. additionwere added dropwise without further heating
  5. extractionThe mixture was extracted with ethyl acetate
  6. extractionthe organic extract
  7. dry with materialwas dried over sodium sulphate
  8. customevaporated
  9. customThe residue was chromatographed on silica gel
  10. washethyl acetate/petroleum ether (1:2) for the elution

Quellen und Nachweise

ORD-Eintrag
ord-f9c8fd77104b4730a33025aa1ec7abef
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05118694

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