Potassium Carbonate → 8-Methoxy-2,3,4,5-tetrahydro-benzo[c]azepin-1-one

HRID 412593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 412593
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=[O:13])=[CH:5][CH:4]=1.[N-:14]=[N+]=[N-].[Na+].C(=O)([O-])[O-].[K+].[K+]>Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][NH:14][C:10](=[O:13])[C:11]=2[CH:12]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one

Produkt 1

HCID 112755298-Methoxy-2,3,4,5-tetrahydro-benzo[c]azepin-1-oneAusbeute 8,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

To a solution of 7-methoxy-1,2,3,4-tetrahydronaphthalen-1-one (5.21 g) in conc. hydrochloric acid (26 ml) was added sodium azide (1.98 g) by portions with ice-cooling, and the mixture was stirred at the same temperature for 2 hours, and then at room temperature for 2 hours. After completion of the reaction, the reaction mixture was poured into ice water and aqueous potassium carbonate was added. The mixture was extracted with chloroform and washed successively with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (ethyl acetate) and dried under reduced pressure to give the title compound (470 mg).

Aufarbeitung

  1. temperaturecooling
  2. waitat room temperature for 2 hours
  3. customAfter completion of the reaction
  4. additionwas added
  5. extractionThe mixture was extracted with chloroform
  6. washwashed successively with water and saturated brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated
  9. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate)
  10. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f8336465c53e460b999a6efa7520545b
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562828B1

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