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Methyl iodide → 7-(5-Chloro-2-methoxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 871975
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 871975
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:24])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([N:12](CO)[C:13]([CH3:21])([CH3:20])[C:14](=[O:19])[N:15]3[CH3:18])=[CH:10][CH:9]=2)[CH:7]=1.CI.[C:27](=[O:30])([O-])[O-].[K+].[K+].[C:33](OCC)(=O)C>CN(C)C=O.O.C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:33])=[C:6]([C:8]2[C:17]([CH2:27][OH:30])=[C:16]3[C:11]([NH:12][C:13]([CH3:21])([CH3:20])[C:14](=[O:19])[N:15]3[CH3:18])=[CH:10][CH:9]=2)[CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 867022207-(5-chloro-2-hydroxyphenyl)-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

Produkt 1

HCID 576717857-(5-Chloro-2-methoxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-oneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 7-(5-chloro-2-hydroxyphenyl)-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 12-1, 1.36 g, 3.92 mmol), methyl iodide (244 μL, 3.92 mmol), and potassium carbonate (1.08 g, 7.81 mmol) was suspended in anhydrous N,N-dimethylformamide (20 mL) and stirred at 50° C. for 1 hour. After cooling down, ethyl acetate (70 mL), diethylether (70 mL), and water (150 mL) were added and partitioned. The organic layer was washed with water (100 mL) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (1.36 g) as a pale yellow amorphous product. (Yield 96%)

Aufarbeitung

  1. temperatureAfter cooling down
  2. custompartitioned
  3. washThe organic layer was washed with water (100 mL) and saturated brine (50 mL) successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-7c888f394da64d22961bdf8a42e680d2
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08975256B2

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