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

HRID 6764

Reaction equation

HRID 6764 reaction equation
[N-:1]=[N+]=[N-].[Na+].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[CH2:12][CH2:11][CH2:10]2.C(=O)([O-])[O-].[K+].[K+]>Cl>[CH3:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[NH:1][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 141126-Methoxy-alpha-tetraloneHCID 33557Sodium Azide

Product 1

HCID 42306097-Methoxy-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Sodium azide (0.37 g) was slowly added in portions to a stirring ice-cold suspension of 6-methoxy-3,4-dihydro-2H-naphthalen-1-one in 10 mL of concentrated hydrochloric acid. The mixture was allowed to slowly warm to room temperature and stirred for 20 h. The mixture was poured onto ice and carefully neutralized with solid potassium carbonate. The resulting mixture was extracted with two 50 mL aliquots of dichloromethane. The organic material was dried over sodium sulfate and the solvent was evaporated. Chromatography (ethyl acetate) gave 0.45 g of 7-methoxy-2,3,4,5-tetrahydrobenzo[c]azepine-1-one.

Workup

  1. additionThe mixture was poured onto ice
  2. extractionThe resulting mixture was extracted with two 50 mL aliquots of dichloromethane
  3. dry with materialThe organic material was dried over sodium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-141213c897394fb3aee98326e828dc45
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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