Potassium Nitrate → 5,5-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine

HRID 401380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401380
[N+:1]([O-:4])([O-])=[O:2].[K+].[CH3:6][C:7]1([CH3:18])[CH2:13][CH2:12][CH2:11][NH:10][C:9]2[CH:14]=[CH:15][CH:16]=[CH:17][C:8]1=2.C([O-])(O)=O.[Na+]>OS(O)(=O)=O>[CH3:6][C:7]1([CH3:18])[CH2:13][CH2:12][CH2:11][NH:10][C:9]2[CH:14]=[C:15]([N+:1]([O-:4])=[O:2])[CH:16]=[CH:17][C:8]1=2

Komponenten

5

Edukt 3

HCID 24434Potassium NitrateHCID 516892Sodium BicarbonateHCID 574702555,5-dimethyl-2,3,4,5-tetrahydro-1H-1-benzazepine

Produkt 1

HCID 574702565,5-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepineAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

At 0° C., KNO3 (0.76 g, 7.54 mmol) was added portionwise to a solution of 5,5-dimethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine (1.1 g, 6.28 mmol) in H2SO4 (15 mL). After stifling 15 min at this temperature, the mixture was poured into ice water, basified with sat. NaHCO3 to pH 8 and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give crude 5,5-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine (1.2 g), which was used directly in the next step without further purification.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3032f45f7d6949cc91f4fff22ba8e27f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741925B2

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