N-(3,4-dihydro-2H-naphthalen-1-ylidene)hydroxylamine → 1,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

HRID 495984

Reaktionsgleichung

Reaktionsgleichung von HRID 495984
[C:1]1(=[N:11]O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-:14].[Na+]>O>[NH:11]1[C:6](=[O:14])[CH2:7][CH2:8][CH2:9][C:10]2[CH:5]=[CH:4][CH:3]=[CH:2][C:1]1=2

Komponenten

4

Edukt 2

HCID 76876N-(3,4-dihydro-2H-naphthalen-1-ylidene)hydroxylamineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1.0 g (6.2 mmole) of 1-tetralone oxime and 10 g polyphosphoric acid was heated at 105° for 1 hr. The warm mixture was poured into 100 mL water with stirring. The pH was carefully adjusted to 6-7 by addition of solid sodium bicarbonate and the mixture was extracted with 60 mL ethyl ether. The organic phase was washed with 10 mL saturated sodium chloride, dried (MgSO4) and concentrated under reduced pressure. The residue was recrystallized from ether/hexane to give 1,3,4,5-Tetrahydro-benzo[b]azepin-2-one, 0.682 g, m.p. 141-142°.

Aufarbeitung

  1. temperaturewas heated at 105° for 1 hr
  2. extractionthe mixture was extracted with 60 mL ethyl ether
  3. washThe organic phase was washed with 10 mL saturated sodium chloride
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-cee0c90f4ab4418986240b79f2d20fb3
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06943169B2

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