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

HRID 388068

Reaktionsgleichung

Reaktionsgleichung von HRID 388068
[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 22646519HCID 22646519, Verbindung

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 saline 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 saline
  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-a5b9a3d025b349dc83b7d96b0902e1fd
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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