Aluminum(III) Chloride → 7-Bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-one

HRID 915185

Reaktionsgleichung

Reaktionsgleichung von HRID 915185
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:15])[CH:11]=[C:12]([CH3:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[CH3:8].[Cl-].[Al+3].[Cl-].[Cl-]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:12]([CH3:13])([CH3:14])[CH2:11][C:10](=[O:15])[NH:9]2)=[CH:6][C:7]=1[CH3:8]

Komponenten

3

Edukt 2

HCID 6451240Aluminum(III) ChlorideHCID 60729710N-(3-Bromo-4-methylphenyl)-3-methyl-2-butenamide

Produkt 1

HCID 219664237-Bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-oneAusbeute 65,7 %

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

To a solution of 3-methyl-but-2-enoic acid (3-bromo-4-methyl-phenyl)-amide (70.0 g, 261 mmol, Example d) at 90° C. was added portion wise, under argon, with vigorous stirring aluminum chloride (52.3 g, 391 mmol) over 1.5 hr. The reaction mixture was stirred for 2 hours at 110-120° C. The reaction mixture was cooled to room temperature and ice-water was carefully added. The solution was extracted with dichloromethane and the organic washed with 2N HCl, water, saturated aqueous NaHCO3, water and brine, dried (Mg2SO4), filtered and evaporated. The residue was crystallized from dichloromethane/hexane to give 46 g of 7-bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-one. The mother liquor was further chromatographed on silica gel(20% ethyl acetate in hexane) to give 6.2 g more of product. (75%). 1H NMR (300 MHz; CDCl3): 1.30 (s, 6 H), 2.33 (s, 3 H), 2.46 (s, 2 H), 7.07 (s, 1 H), 7.10 (s, 1 H), 9.87 (br s, 1 H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe solution was extracted with dichloromethane
  3. washthe organic washed with 2N HCl, water, saturated aqueous NaHCO3, water and brine
  4. dry with materialdried (Mg2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from dichloromethane/hexane

Quellen und Nachweise

ORD-Eintrag
ord-8a86a5a67dc54d78a78f4f0e41046c4d
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265139B2

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