6H-Dibenz[b,d]azepin-6-one, 5,7-dihydro-5-methyl-

20011-90-9

74-88-4

209984-30-5

Step A - Synthesis of 7-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one: Sodium hydride (0.295 g, 7.46 mmol) and 9.0 mL of anhydrous DMF were added to a dry round-bottomed flask, and stirred until completely dissolved. Subsequently, 5,7-dihydro-6H-dibenzo[b,d]azepin-6-one (1.3 g, 6.22 mmol) was added, and the reaction mixture was stirred at 60 °C for 1 hour. Then, iodomethane (1.16 mL, 18.6 mmol) was slowly added dropwise and stirring was continued for 17 h under light protection. After completion of the reaction, the mixture was cooled to room temperature, diluted with a mixture of dichloromethane and water, washed sequentially with NaHSO4 solution and water, and the organic phase was dried with anhydrous Na2SO4. After concentration under reduced pressure, it was purified by fast column chromatography (silica gel, chloroform as eluent) to afford 0.885 g (63% yield) of the target compound, 5-methyl-5H-dibenz[b,d]azepin-6(7H)-one, as a colorless solid. Nuclear Magnetic Resonance Hydrogen Spectroscopy (1H-NMR, CDCl3) data: δ= 7.62 (d, 2H), 7.26-7.47 (m, 6H), 3.51 (m, 2H), 3.32 (s, 3H). Elemental analysis: C15H13NO (molecular weight = 223.27); mass spectrum (MH+) 223. calculated values: C, 80.69; H, 5.87; N, 6.27. measured values: C, 80.11; H, 5.95; N, 6.23.