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

HRID 495984

Reaction equation

HRID 495984 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-cee0c90f4ab4418986240b79f2d20fb3
Source dataset
uspto-grants-2005_09
Patent number
US06943169B2

Linked notes

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