Water → Ethyl 1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 341028

Reaktionsgleichung

Reaktionsgleichung von HRID 341028
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[C:3]1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1.O>CN(C)C=O>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2](=[O:1])[C:3]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4]2)=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 699934-Methyloxybenzyl chlorideHCID 220876Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate

Produkt 1

HCID 53396422Ethyl 1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate (3.17 g, 14.6 mmol) and 4-methoxybenzylchloride (2.18 mL, 16.0 mmol, 1.1 equiv) were combined in N,N-dimethylformamide (50 mL) and stirred at ambient temperature for 72 hours. The mixture was poured into water (500 mL) and extracted with dichloromethane (2×250 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was treated with water (500 mL), hexanes (500 mL) and ethyl acetate (500 mL) and aged for 30 minutes. The mixture was filtered and the solid was dissolved in dichloromethane (500 mL) and combined with the filtrate. The filtrate was partitioned and the aqueous layer was discarded. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

Aufarbeitung

  1. extractionextracted with dichloromethane (2×250 mL)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionThe residue was treated with water (500 mL), hexanes (500 mL) and ethyl acetate (500 mL)
  6. waitaged for 30 minutes
  7. filtrationThe mixture was filtered
  8. dissolutionthe solid was dissolved in dichloromethane (500 mL)
  9. customThe filtrate was partitioned
  10. dry with materialThe organic layer was dried with sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ba5cf9c3bad2420e9d31e65fd249ca1e
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895580B2

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