Sulfuric Acid → 2H-3-Benzazepin-2-one, 1,3,4,5-tetrahydro-

HRID 1761026Notes

Reaction equation

HRID 1761026 reaction equation
[N-:1]=[N+]=[N-].[Na+].[CH2:5]1[C:14](=[O:15])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1.S(=O)(=O)(O)O>C(O)(=O)C.C(OCC)(=O)C>[CH2:13]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][NH:1][C:14]1=[O:15]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 682662-Tetralone

Product 1

HCID 2042322H-3-Benzazepin-2-one, 1,3,4,5-tetrahydro-

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

While maintaining the temperature of the reaction mixture below 65° C., NaN3 (13.35 g; 205.2 mmol) is added in small portions to a solution, heated beforehand to 55° C., of β-tetralone (25 g; 171 mmol) in a mixture of 150 ml of glacial acetic acid and concentrated sulphuric acid (33.39 g; 342 mmol; 18.25 ml). Stirring is then carried out for 8 hours at 70° C. After returning to ambient temperature, the reaction mixture is poured onto ice and diluted with ethyl acetate. After extracting the organic phase, drying over magnesium sulphate and concentrating, the residue obtained is purified by chromatography on silica gel (eluant ethyl acetate) to yield the expected compound.

Workup

  1. additionis added in small portions to a solution
  2. customAfter returning to ambient temperature
  3. additionthe reaction mixture is poured onto ice
  4. extractionAfter extracting the organic phase
  5. dry with materialdrying over magnesium sulphate
  6. concentrationconcentrating
  7. customthe residue obtained
  8. customis purified by chromatography on silica gel (eluant ethyl acetate)

Sources & evidence

ORD record
ord-b816c698683344219c10a8334150faa0
Source dataset
uspto-grants-2005_01
Patent number
US06846833B2

Reaction notes

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