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Water → 7-(5-Chloro-2-hydroxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 1038477
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1038477
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:25]=[C:24]2[C:11]([O:12][C:13](=[O:30])[C:14]3[C:23]2=[CH:22][CH:21]=[C:20]2[C:15]=3[N:16]([CH3:29])[C:17](=[O:28])[C:18]([CH3:27])([CH3:26])[NH:19]2)=[CH:10][CH:9]=1.C(OCC)(=O)C.O>O1CCCC1.[Cl-].[Na+].O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([OH:12])=[C:24]([C:23]2[C:14]([CH2:13][OH:30])=[C:15]3[C:20]([NH:19][C:18]([CH3:26])([CH3:27])[C:17](=[O:28])[N:16]3[CH3:29])=[CH:21][CH:22]=2)[CH:25]=1
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Komponenten

7

Edukt 4

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 21226445Aluminium lithium hydrideHCID 576717409-Chloro-2,2,4-trimethyl-1,4-dihydro-2H-6-oxa-1,4-diazachrysen-3,5-dione

Produkt 1

HCID 247808507-(5-Chloro-2-hydroxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-oneAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

Lithium aluminium hydride (442 mg, 11.7 mmol) was suspended in anhydrous tetrahydrofuran (10 mL) under nitrogen atmosphere. An anhydrous tetrahydrofuran solution (40 mL) of 9-chloro-2,2,4-trimethyl-1,4-dihydro-2H-6-oxa-1,4-diazachrysen-3,5-dione (Reference Compound No. 11-1, 1.99 g, 5.81 mmol) was added dropwise thereto at −10° C. and stirred for 10 minutes at the same temperature. After ethyl acetate (1 mL) and water (1 mL) were added thereto successively, ethyl acetate (300 mL) and saturated brine (300 mL) were added and partitioned. The organic layer was washed with saturated brine (150 mL), 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 (1.38 g) as a pale yellow solid. (Yield 69%)

Aufarbeitung

  1. custompartitioned
  2. washThe organic layer was washed with saturated brine (150 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c7a1062ecb5a4918b5300ce76b3ac932
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08551991B2

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