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

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

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.