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Benzyl Bromide → Phenyl 7-benzyloxy-4-oxo-1,4-dihydro-6-quinolinecarboxylate

HRID 1433696
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1433696
CC1(C)O[C:6](=[O:8])[C:5](=[CH:9][NH:10][C:11]2[CH:25]=[CH:24][C:14]([C:15]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:16])=[C:13]([OH:26])[CH:12]=2)C(=O)O1.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)C.O1CCCC1>CN(C)C=O.C(O)C.CCCCCC.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.C(OCC)C.O>[CH2:29]([O:26][C:13]1[CH:12]=[C:11]2[C:25]([C:6](=[O:8])[CH:5]=[CH:9][NH:10]2)=[CH:24][C:14]=1[C:15]([O:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:16])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

11

Edukt 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21868444Ether tetrahydrofuranHCID 22936474Phenyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-hydroxybenzoate

Produkt 1

HCID 22936353Phenyl 7-benzyloxy-4-oxo-1,4-dihydro-6-quinolinecarboxylateAusbeute 10.766,7 %

Reagenzien, Katalysatoren, Lösungsmittel

6
HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8058HexaneLösungsmittelHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Lösungsmittel

Versuchsvorschrift

Phenyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-hydroxybenzoate (11.5 g, 0.030 mmol), benzyl bromide (5.64 g, 0.033 mmol) and potassium carbonate (4.56 g, 0.033 mmol) were stirred in dimethylformamide (45 ml) at 80° C. for 3 hours. The reaction solution was distributed between a diethyl ether-tetrahydrofuran mixed solvent and water, the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, and the drying agent was filtered out and the filtrate distilled off under reduced pressure. The obtained crude product was suspended in ethanol, the suspension was diluted with hexane, and the crystals were filtered out, washed with hexane and blow-dried to obtain white crystals. The crystals were then heated and stirred for 1 hour in Dowtherm A (50 ml) at 200° C. After allowing the reaction solution to cool to room temperature, diethyl ether (25 ml) was added and the mixture was further stirred overnight. The precipitated crystals were filtered out, washed with diethyl ether and blow-dried to obtain the title compound (1.20 g, 3.23 mmol, 11%) as white crystals.

Aufarbeitung

  1. washthe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered out
  4. distillationthe filtrate distilled off under reduced pressure
  5. customThe obtained crude product
  6. filtrationthe crystals were filtered out
  7. washwashed with hexane
  8. customblow-dried
  9. customto obtain white crystals
  10. temperatureThe crystals were then heated
  11. filtrationThe precipitated crystals were filtered out
  12. washwashed with diethyl ether
  13. customblow-dried

Quellen und Nachweise

ORD-Eintrag
ord-6c6cd9f53a1346119146fd4124c2c396
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07612092B2

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