Hydrochloric Acid → 4-(5-Chloro-3-phenyl-1,6-naphthyridin-2-yl)benzaldehyde

HRID 1678761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678761
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:6]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]3OCC[O:19]3)=[CH:14][CH:13]=1)=[N:7]2.Cl>O1CCOCC1>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:6]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][CH:13]=1)=[N:7]2

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 575007255-Chloro-2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-1,6-naphthyridine

Produkt 1

HCID 575007324-(5-Chloro-3-phenyl-1,6-naphthyridin-2-yl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-3 (16 g, 41.1 mMol) in anhydrous 1,4-dioxane (75 mL) at 0° C. was added 3N HCl (27 mL). The reaction was then allowed to reach room temperature and was stirred for around 3 hours. Upon completion, the reaction was quenched with saturated NaHCO3 solution to reach a pH of >7. The product was extracted into ethyl acetate (3×150 mL). The combined organic layers were washed with brine, dried with Na2SO4 and MgSO4, filtered and concentrated in vacuo to yield 4-(5-chloro-3-phenyl-1,6-naphthyridin-2-yl)benzaldehyde 9-1 as a tan solid. LC/MS (M+1) calculated: 345.8; observed: 345.0

Aufarbeitung

  1. customto reach room temperature
  2. customUpon completion, the reaction was quenched with saturated NaHCO3 solution
  3. extractionThe product was extracted into ethyl acetate (3×150 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried with Na2SO4 and MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-09d446cfe6534a74841095f904a4c87f
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008317B2

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