Chloride → 6-Chloro-3-phenyl-1,5-naphthyridin-2(1H)-one

HRID 42371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 42371
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=O)[C:5]([NH:10][C:11](=[O:17])OC(C)(C)C)=[CH:4][CH:3]=1.[Cl-].[CH2:19]1[CH2:29][CH2:28]N2[C:22](=NCCC2)[CH2:21][CH2:20]1.[CH2:30]1COCC1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:10][C:11](=[O:17])[C:30]([C:22]1[CH:21]=[CH:20][CH:19]=[CH:29][CH:28]=1)=[CH:8]2

Komponenten

6

Edukt 4

HCID 312ChlorideHCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58216578tert-Butyl (6-chloro-2-formylpyridin-3-yl)carbamate

Produkt 1

HCID 665249196-Chloro-3-phenyl-1,5-naphthyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of tert-butyl (6-chloro-2-formylpyridin-3-yl)carbamate (1-4) (5 g, 19.5 mmol), phenylacethyl chloride (3.3 g, 21.4 mmol), and DBU (9.8 g, 39 mmol) in THF (215 mL) was stirred at room temperature for 2 days and at 100° C. for overnight. The mixture was diluted with CHCl3, washed with water and brine, dried (MgSO4), filtered, and the solvent was removed under reduced pressure. To the residue was added CHCl3, and the resulting solid was collected by filtration to give 6-chloro-3-phenyl-1,5-naphthyridin-2(1H)-one (7-1) as colorless solid.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. additionTo the residue was added CHCl3
  6. filtrationthe resulting solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-9e8b644fdd414a4ab4ff50a1954391a0
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536193B2

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