Potassium Carbonate → 7-Hydroxy-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one

HRID 393563Notes

Reaction equation

HRID 393563 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[N-:13]=[N+]=[N-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CS(O)(=O)=O>[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[NH:13][CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 107259837-Hydroxy-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-hydroxy-1-tetralone (6.5 g) in methanesulfonic acid (140 ml) was added sodium azide (3.4 g) under cooling with ice and the mixture was stirred for 30 minutes at 0° C. and for 15 hours at room temperature. The reaction mixture was poured into ice-water and thereto was added potassium carbonate to alkalify and was extracted with methylene chloride. The organic layer was washed with water, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride successively, dried over anhydrous magnesium sulfate and was concentrated to give the title compound having the following physical data as a crude product. The crude product was used in the next reaction without further purification.

Workup

  1. temperatureunder cooling with ice
  2. extractionwas extracted with methylene chloride
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride successively, dried over anhydrous magnesium sulfate
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-04c783680bae4c01a46900ca440458c2
Source dataset
uspto-grants-2004_10
Patent number
US06809092B2

Reaction notes

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