Ethyl Acetate → Methyl 4-(4-amino-3-chlorophenoxy)-7-(benzyloxy)-6-quinolinecarboxylate

HRID 1010309

Reaktionsgleichung

Reaktionsgleichung von HRID 1010309
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[Cl:9].[H-].[Na+].[CH2:12]([O:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24](Cl)=[CH:25][CH:26]=[N:27]2)=[CH:22][C:21]=1[C:31]([O:33][CH3:34])=[O:32])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OCC)(=O)C>CS(C)=O.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:24]2[C:23]3[C:28](=[CH:29][C:20]([O:19][CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[C:21]([C:31]([O:33][CH3:34])=[O:32])[CH:22]=3)[N:27]=[CH:26][CH:25]=2)=[CH:4][C:3]=1[Cl:9]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 871844-Amino-3-chlorophenolHCID 22936661Methyl 7-(benzyloxy)-4-chloro-6-quinolinecarboxylate

Produkt 1

HCID 22936786Methyl 4-(4-amino-3-chlorophenoxy)-7-(benzyloxy)-6-quinolinecarboxylateAusbeute 73,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

After dissolving 4-amino-3-chlorophenol (2.22 g, 15.45 mmol) in dimethylsulfoxide (40 ml), sodium hydride (618 mg, 15.45 mmol) was gradually added at room temperature and the mixture was stirred for 30 minutes. Methyl 7-(benzyloxy)-4-chloro-6-quinolinecarboxylate (4.05 g, 12.36 mmol) was added, and the mixture was heated at 100° C. for 2 hours while stirring. Upon cooling to room temperature, the reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off and subjected to silica gel column chromatography (eluent-ethyl acetate), the fraction containing the target substance was concentrated, suspended in ethyl acetate and diluted with hexane, and the crystals were filtered out and blow-dried to obtain the title compound (3.938 g, 9.06 mmol, 73.3%) as light brown crystals.

Aufarbeitung

  1. additionwas gradually added at room temperature
  2. stirringwhile stirring
  3. temperatureUpon cooling to room temperature
  4. washthe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. additionthe fraction containing the target substance
  8. concentrationwas concentrated
  9. additiondiluted with hexane
  10. filtrationthe crystals were filtered out and
  11. customblow-dried

Quellen und Nachweise

ORD-Eintrag
ord-fa67e8974cf340d78dd7f3bd0ffa168d
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973160B2

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