Synthesis of Agomelatine by One-pot Catalytic Hydrogenation and Acetylation with NiO

• Published in: Journal of Wuhan University of Technology. Materials science edition Vol. 34; no. 2; pp. 453 - 458
• Main Authors: Yu, Zhijun, Cheng, Zhengzai, Xie, Cong, Zeng, Sheng, Deng, Haiying, Liu, Panpan, Hu, Hai, Li, Guangyao, Ding, Ling, Gauthier, Mario, Li, Shiqian
• Format: Journal Article
• Language: English
• Published: Wuhan Wuhan University of Technology 01.04.2019
• Subjects: Chemistry and Materials Science; Materials Science; Organic Materials; 7-Methoxy-1-naphthylacetonitrile; catalytic hydrogenation; agomelatine; N-[2- (7-Methoxy-1-naphthyl)ethyl]acetamide; homogeneous precipitation method; nano-NiO
• ISSN: 1000-2413; 1993-0437
• DOI: 10.1007/s11595-019-2073-3

Nano-NiO and bulk NiO were prepared from Ni(AC) 2 ·4H 2 O by coordination precipitation using aqueous ammonia and by a solid state reaction, respectively. The nickel oxide particles were characterized by X-ray Diffraction (XRD) and scanning electron microscopy (SEM). The results indicate that nano-sized NiO has a crystal phase with a standard face-centered cubic lattice structure, with a mean particle diameter of about 10 nm. The evaluation of the activity of nickel oxide nanoparticles in the catalytic hydrogenation of 7-methoxy-1-naphthylacetonitrile was carried out. The results demonstrate the efficient synthesis of the title compound by a one-pot catalytic hydrogenation and acetylation with NiO. The NiO nanoparticles displayed superior catalytic activity in the synthesis of agomelatine in the one-pot reaction.The total yield of agomelatine is over 81.8% with a purity of 99.2%, as determined by HPLC. The structure of agomelatine was confirmed by IR, MS, and 1H NMR analysis.