Ethanol → 4-[(7-Oxo-7,8-dihydro[1,8]naphthyridin-4-yl)oxy]aniline

HRID 1010184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010184
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[C:18]3[CH:17]=[CH:16][C:15](=[O:19])[NH:14][C:13]=3[N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].CN(C)C=O.C(O)C>[Fe].O>[O:19]=[C:15]1[NH:14][C:13]2[N:12]=[CH:11][CH:10]=[C:9]([O:8][C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:21][CH:20]=3)[C:18]=2[CH:17]=[CH:16]1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 229368804-(4-Nitrophenoxy)-7-oxo-7,8-dihydro[1,8]naphthyridine

Produkt 1

HCID 589313574-[(7-Oxo-7,8-dihydro[1,8]naphthyridin-4-yl)oxy]aniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

4-(4-Nitrophenoxy)-7-oxo-7,8-dihydro[1,8]naphthyridine (156 mg), iron powder (300 mg), ammonium chloride (600 mg), dimethylformamide (2 ml), ethanol (1 ml) and water (1 ml) were stirred at 100° C. for 20 minutes. The mixture was filtered with celite, and then water and ethyl acetate were added for extraction. The organic layer was washed 4 times with aqueous ammonium chloride solution and then dried over magnesium sulfate. The drying agent was filtered off and the solvent was distilled off under reduced pressure to obtain 30 mg of the target substance as a light yellow solid.

Aufarbeitung

  1. filtrationThe mixture was filtered with celite
  2. additionwater and ethyl acetate were added for extraction
  3. washThe organic layer was washed 4 times with aqueous ammonium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain 30 mg of the target substance as a light yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-873b8c146d454f79ad5f46b805b70a46
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973160B2

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