Potassium Carbonate → 7-amino-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one

HRID 2088744Notes

Reaction equation

HRID 2088744 reaction equation
[N-:1]=[N+]=[N-].[Na+].[NH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10][CH2:9]2.C(=O)([O-])[O-].[K+].[K+]>Cl>[NH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[NH:1][CH2:11][CH2:10][CH2:9][C:8]=2[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 3395376-Amino-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 598623477-amino-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-oneYield 50.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
40 °C

Procedure

With cooling with ice, 890 mg of sodium azide was added to a concentrated hydrochloric acid (30 mL) solution of 2 g of 6-amino-1,2,3,4-tetrahydronaphthalen-1-one, and stirred at 40° C. 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 basic silica gel column chromatography (chloroform/methanol) to obtain 1.1 g of the entitled compound as a colorless 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 basic silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-2b90577794df48adb579d8bd9fc228c2
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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