Nitric Acid → HCID 70224229, Verbindung

HRID 1384269Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1384269
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[N+:11]([O-:12])=[C:10]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:9]2=[CH:8][C:7]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[OH-].[Na+]>>[CH3:5][C:6]1[N+:11]([O-:12])=[C:10]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:9]2=[C:8]([N+:1]([O-:4])=[O:2])[C:7]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Komponenten

4

Edukt 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 70224223HCID 70224223, Verbindung

Produkt 1

HCID 70224229HCID 70224229, VerbindungAusbeute 92,4 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Fuming nitric acid (27.0 ml) was added dropwise to ethyl 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate N-oxide (3.10 g, 12.4 mmol) at 0° C., and the mixture was stirred at 90° C. for 2 hours. After cooling, the reaction solution was poured into ice water, mixed with 2 N sodium hydroxide aqueous solution and extracted with chloroform, and the thus obtained organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. After evaporation of the solvent under reduced pressure, the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=40:1) to obtain the title compound (3.38 g, 92.4%) as pale yellow powder.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with chloroform
  3. washthe thus obtained organic layer was washed with water and saturated brine in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter evaporation of the solvent under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (chloroform:methanol=40:1)

Quellen und Nachweise

ORD-Eintrag
ord-e172ef55557049279b148bb2cd118a60
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06258829B1

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