Cl.[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[C:11]2[CH2:14][CH2:15][NH2:16])=[CH:6][CH:5]=1.[C:17]([O-])(=[O:19])[CH3:18].[Na+].C(OC(=O)C)(=O)C.O>C(O)C>[CH3:18][C:17]([NH:16][CH2:15][CH2:14][C:11]1[C:12]2[CH:13]=[C:4]([O:3][CH3:2])[CH:5]=[CH:6][C:7]=2[CH:8]=[CH:9][CH:10]=1)=[O:19]The compound V (6.0 g, 0.03 mol) produced as described above and sodium acetate (3.4 g) were dissolved in 70 ml of ethanol, and acetic anhydride (3.4 g, 0.033 mol) was added. The reaction solution was heated and refluxed for one hour. After cooling, about 100 ml of water was added, and the mixture was extracted with ethyl acetate (50 ml*3). The organic phases were combined, dried with anhydrous magnesium sulfate, and filtered to remove the drying agent. The filtrate was concentrated under reduced pressure, to give a solid. The solid was recrystallized in a 2:1 toluene/n-hexane mixture, to produce 5.3 g of agomelatine. The yield was 86.7%. The melting point was 107-109° C. (in Literature [2], 109° C.).
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