HCID 70224223, Verbindung → HCID 21186674, Verbindung

HRID 1384265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1384265
[CH3:1][C:2]1[N+:7]([O-])=[C:6]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:5]2=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(OC(=O)C)(=O)C>[C:14]([O:16][CH:9]1[C:6]2=[N:7][C:2]([CH3:1])=[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:4]=[C:5]2[CH2:13][CH2:12][CH2:11][CH2:10]1)(=[O:15])[CH3:3]

Komponenten

3

Edukt 1

HCID 70224223HCID 70224223, Verbindung

Produkt 1

HCID 21186674HCID 21186674, VerbindungAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

Ethyl 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate N-oxide (1.00 g, 4.02 mmol) was dissolved in acetic anhydride (7.0 ml) and heated under reflux for 1.5 hours. After cooling, excess acetic anhydride was evaporated under reduced pressure, the thus obtained residue was mixed with ice water and saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate, and the resulting organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (ether:hexane=1:1) to obtain the title compound (482.5 mg, 45.8%) as pale brown oil.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling
  4. customexcess acetic anhydride was evaporated under reduced pressure
  5. additionthe thus obtained residue was mixed with ice water and saturated sodium bicarbonate aqueous solution
  6. extractionextracted with ethyl acetate
  7. washthe resulting organic layer was washed with water and saturated brine in that order
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe resulting residue was purified by a silica gel column chromatography (ether:hexane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c4dc63af7d0241969ffa3a49b100cff4
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06258829B1

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