1-Tetralone → 2,3,4,5-Tetrahydro-benzo[c]azepin-1-one

HRID 2088731Notes

Reaction equation

HRID 2088731 reaction equation
[N-:1]=[N+]=[N-].[Na+].[CH2:5]1[CH2:15][C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1.C(=O)([O-])[O-].[K+].[K+]>Cl>[C:13]1(=[O:14])[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:15][NH:1]1

Participants

5

Reactant 3

HCID 107241-TetraloneHCID 11430Potassium CarbonateHCID 33557Sodium Azide

Product 1

HCID 112406552,3,4,5-Tetrahydro-benzo[c]azepin-1-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

With cooling with ice, 2.6 g of sodium azide was added to a concentrated hydrochloric acid (60 mL) solution of 5 mL of alpha-tetralone, and stirred at room temperature for 15 hours. The reaction liquid was poured into ice water, and neutralized with potassium carbonate. This was extracted with chloroform, and the organic layer was washed with saturated saline water and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the crude product was purified through silica gel column chromatography (chloroform/methanol) to obtain 2.3 g of the entitled compound as a yellow solid.

Workup

  1. customThe reaction liquid
  2. extractionThis was extracted with chloroform
  3. washthe organic layer was washed with saturated saline water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe crude product was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-eeb231ce04fb4f78809f9c75cbd3214b
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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