O-Methylhydroxylamine → 3-Amino-4-nitropyridine

HRID 265634

Reaktionsgleichung

Reaktionsgleichung von HRID 265634
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].CO[NH2:12].CC(C)([O-])C.[K+].[Cl-].[NH4+]>CN(C=O)C.[Cl-].[Zn+2].[Cl-].C(OCC)(=O)C.CCCCCC>[NH2:12][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Komponenten

8

Edukt 4

HCID 4113O-MethylhydroxylamineHCID 25517Ammonium ChlorideHCID 707344-NitropyridineHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 5869433-Amino-4-nitropyridineAusbeute 25,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 6228DimethylformamideLösungsmittel2×HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

4-Nitropyridine (124 mg, 1 mmol) and O-methylhydroxylamine (71 mg, 1.5 mmol) were dissolved in DMF (2 ml), and a resulting solution was added dropwise to a DMF solution (3 ml) containing potassium tert-butoxide (336 mg, 3 mmol) and zinc (II) chloride (136 mg, 1 mmol) at 25° C. After completion of the addition, the resulting mixture was at 25° C. for one hour and an aqueous saturated ammonium chloride solution (50 ml) was added, followed by extraction with ethyl acetate (80 ml). A resulting organic layer was dried over anhydrous magnesium sulfate, and then isolated and purified by subjecting to silica gel thin layer chromatography (eluent: ethyl acetate/hexane=1/1] to obtain 35 mg of 3-amino-4-nitropyridine (yield: 25%).

Aufarbeitung

  1. additionAfter completion of the addition
  2. extractionfollowed by extraction with ethyl acetate (80 ml)
  3. dry with materialA resulting organic layer was dried over anhydrous magnesium sulfate
  4. customisolated
  5. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-f352db06847e43c7b3aa6d376b97850d
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648496

Verknüpfte Notizen

Wird geladen…