Ethyl Acetate → 4-(4-Amino-2,3-dimethylphenoxy)-7-benzyloxy-6-cyanoquinoline

HRID 853595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 853595
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[C:3]=1[CH3:10].[H-].[Na+].[CH2:13]([O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25](Cl)=[CH:26][CH:27]=[N:28]2)=[CH:23][C:22]=1[C:32]#[N:33])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)(=O)C>CS(C)=O.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:25]2[C:24]3[C:29](=[CH:30][C:21]([O:20][CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[C:22]([C:32]#[N:33])[CH:23]=3)[N:28]=[CH:27][CH:26]=2)=[C:4]([CH3:9])[C:3]=1[CH3:10]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 765424-HydroxyxylidineHCID 226465197-Benzyloxy-4-chloro-6-cyanoquinoline

Produkt 1

HCID 229365164-(4-Amino-2,3-dimethylphenoxy)-7-benzyloxy-6-cyanoquinolineAusbeute 42,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-Amino-2,3-xylenol (2.80 g) purchased from Tokyo Chemical Industries was dissolved in dimethylsulfoxide (15 ml), and after gradually adding sodium hydride (816 mg) at room temperature, the mixture was stirred for 20 minutes. 7-Benzyloxy-4-chloro-6-cyanoquinoline (3.0 g) was added, and the mixture was heated at 100° C. for 4 hours while stirring. After cooling to room temperature, the reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with water, 1N aqueous sodium hydroxide and saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained crude product was washed with ethyl acetate to obtain the title compound (1.72 g) as light brown crystals.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washthe organic layer was washed with water, 1N aqueous sodium hydroxide and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe obtained crude product
  6. washwas washed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-543e58c0238540b599e1365bd51cb283
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253286B2

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