Hydrochloric Acid → 8-chloro-9-hydroxy-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one

HRID 1398459Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398459
[Cl:1][C:2]1[C:3](I)=[CH:4][C:5]2[C:14]3[C:9](=[C:10]([CH3:15])[N:11]=[CH:12][CH:13]=3)[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[CH:18]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[OH-:34].[K+].Cl>CS(C)=O.O.[Cu]I>[Cl:1][C:2]1[C:3]([OH:34])=[CH:4][C:5]2[C:14]3[C:9](=[C:10]([CH3:15])[N:11]=[CH:12][CH:13]=3)[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[CH:18]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 13181,10-PhenanthrolineHCID 14797Potassium HydroxideHCID 867103578-chloro-9-iodo-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one

Produkt 1

HCID 867104338-chloro-9-hydroxy-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-oneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the stirred solution of 8-chloro-9-iodo-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (1.0 g, 2.60 mmol) in DMSO (5 mL) and Water (5 mL) in an inert atmosphere were added copper(I) iodide (0.050 g, 0.260 mmol) followed by 1,10-phenanthroline (0.047 g, 0.260 mmol) and KOH (2.188 g, 39.0 mmol). The reaction mixture was heated to 100° C. for 16 h and monitored by LC/MS. Upon completion, the reaction mixture was cooled and pH adjusted to between 3 to 4 with 1 N HCl. The reaction mixture was diluted with 50 mL of water and extracted with 80 mL of dichloromethane. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 8-chloro-9-hydroxy-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (0.6 g, 2.053 mmol, 79% crude yield) as a green solid. The material was carried on without further purification. LC/MS (ESI) m/e 273.0 [(M)−, calcd for C14H10ClN2O2 273.05]; LC/MS retention time (method C): tR=2.06 min.

Aufarbeitung

  1. temperatureUpon completion, the reaction mixture was cooled
  2. extractionextracted with 80 mL of dichloromethane
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-599460acd52e4f2780eb5327347847ba
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901305B2

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